Bromomethylcyclopropane → 6-[(Cyclopropylmethyl)sulfanyl]pyridine-3-carboxylic acid

HRID 341557Notes

Reaction equation

[SH:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.Br[CH2:12][CH:13]1[CH2:15][CH2:14]1>>[CH:13]1([CH2:12][S:1][C:2]2[N:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=2)[CH2:15][CH2:14]1

Participants

Reactant 2

HCID 81503Bromomethylcyclopropane

HCID 1785245186-sulfanylpyridine-3-carboxylic acid

Product 1

HCID 613050966-[(Cyclopropylmethyl)sulfanyl]pyridine-3-carboxylic acidYield 77.3%

Procedure

6-[(Cyclopropylmethyl)sulfanyl]pyridine-3-carboxylic acid was prepared from 6-sulfanylpyridine-3-carboxylic acid (0.5 g, 3.22 mmol) and (bromomethyl)cyclopropane (0.44 g, 3.22 mmol) according to the method described for Intermediate 276 to afford the title compound (0.521 g, 61%). Method B HPLC-MS: MH+ requires m/z=210 Found: m/z=210, Rt=1.77 min (79%).

Sources & evidence

ORD record: ord-be2142de39f84b53b4c7f29d0edc9167
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895733B2

Reaction notes

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