Diethyl Carbonate → Ethyl 2-(4-broMopyridin-2-yl)acetate

HRID 705332Notes

Reaction equation

HRID 705332 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][N:3]=1.[C:9](=O)([O:13]CC)[O:10][CH2:11][CH3:12]>>[Br:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([CH2:1][C:9]([O:10][CH2:11][CH3:12])=[O:13])[CH:7]=1

Participants

3

Reactant 2

HCID 7766Diethyl CarbonateHCID 27628354-Bromo-2-methylpyridine

Product 1

HCID 53419398Ethyl 2-(4-broMopyridin-2-yl)acetate

Procedure

Scheme 15 illustrates a synthesis of the indolizine-1-carboxylate ring system. In a similar manner to that in the literature (Parrick J, et al. J. Chem. Research (Synopses) 1990; 64-65), 2-methyl-4-bromopyridine may be deprotonated and treated with diethyl carbonate to give ethyl 2-(4-bromopyridin-2-yl)acetate (84). The ester (84) may then be treated with a bromoacetophenone (e.g. 2-bromo-1-(4-methoxyphenyl)ethanone) to give the indolizine ring system (85). The ester may be converted to the carboxaldehyde (86) by methods known to those skilled in the art. The aldehyde may be manipulated to the nitrile (87); and (86) and (87) both further transformed as described hereinabove.

Workup

  1. customa synthesis of the indolizine-1-carboxylate ring system

Sources & evidence

ORD record
ord-f9780cc1d14040e5ac56e73f5ff6dd42
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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