2-Bromopyridine → Pyridine, 2-(trimethylstannyl)-

HRID 524380Notes

Reaction equation

HRID 524380 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:8][Sn:9]([CH3:17])([CH3:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.Br[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:21][CH:20]=1>>[CH3:8][Sn:9]([CH3:17])([CH3:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 79732-BromopyridineHCID 7020609Ethyl 2-(4-bromophenyl)acetateHCID 11021057Pyridine, 2-(trimethylstannyl)-

Product 2

HCID 11021057Pyridine, 2-(trimethylstannyl)-Yield 45%HCID 85828232Ethyl 4-(2-pyridinyl)benzeneacetate

Procedure

The older known synthesis as described in EP 1244641 B1 on page 21 starts from 2-bromopyridine. In step 1 the 2-trimethylstannanylpyridine is prepared in a 45 to 50% yield (of the theory). The 2-trimethylstannanylpyridine is subsequently reacted with ethyl (4-bromophenyl)acetate in order to obtain the ethyl (4-pyridin-2-ylphenyl)acetate in a 75% yield. In the third step the ethyl (4-pyridin-2-ylphenyl)acetate is saponified to the (4-pyridin-2-ylphenyl)acetic acid with about 95% yield of theory. Consequently, the state of the art synthesis as shown below

Workup

  1. customsynthesis

Sources & evidence

ORD record
ord-83cfa4664b6e4eb883e605beabbdaf8c
Source dataset
uspto-grants-2016_05
Patent number
US09340535B2

Reaction notes

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