-CH3 H3C. CH3 Piquindone ) Complete the blank boxes by filling in the missing structures. ii) Write (by the reaction arrows) the missing reagents for Steps 3, 4 and 5. STEP 1 H3C CO2Et NaOEt, ELOH CO>Et room temp STEP 2 1. NABH4 2. base (same transformation can also be achieved with acid) H3C. `OEt steps STEP 3 H3C, reagents??? `CH3 EtO OEt STEP 4 STEP 5 H3C, H3C reagents??? NaOEt, EtOH STEP 6 Br STEP 7 reagents??? Piquindone

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter16: Synthesis Workshop 1
Section: Chapter Questions
Problem 10CTQ
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In the image is a synthesis of the dopamine D2 recpetor antagonist, Piquindone.

i) Complete the blank boxes by filling in the missing structures.

ii) Write the missing reagents for steps 3, 4, 5 and 7.

CH3
H3C
-CH3
Piquindone
) Complete the blank boxes by filling in the missing structures.
ii) Write (by the reaction arrows) the missing reagents for Steps 3, 4 and 5.
STEP 1
H3C.
CO2Et
NaOEt, EtOH
.CO2Et
room temp
STEP 2
1. NABH4
2. base
(same transformation can
also be achieved with acid)
H3C.
OEt
steps
STEP 3
H3C.
reagents???
CH3
EtO
OEt
STEP 4
STEP 5
H
H3C.
H3C.
N.
reagents???
NaOEt, EtOH
STEP 6
Br
STEP 7
reagents???
Piquindone
Transcribed Image Text:CH3 H3C -CH3 Piquindone ) Complete the blank boxes by filling in the missing structures. ii) Write (by the reaction arrows) the missing reagents for Steps 3, 4 and 5. STEP 1 H3C. CO2Et NaOEt, EtOH .CO2Et room temp STEP 2 1. NABH4 2. base (same transformation can also be achieved with acid) H3C. OEt steps STEP 3 H3C. reagents??? CH3 EtO OEt STEP 4 STEP 5 H H3C. H3C. N. reagents??? NaOEt, EtOH STEP 6 Br STEP 7 reagents??? Piquindone
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