Sodium Carbonate → 5-(6-Methoxy-3-pyridinyl)-2-thiophenecarboxylic acid

HRID 551281Notes

Reaction equation

HRID 551281 reaction equation
Br[C:2]1[S:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.Cl.[CH3:11][O:12][C:13]1[N:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:11][O:12][C:13]1[N:18]=[CH:17][C:16]([C:2]2[S:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 3491155-Bromothiophene-2-carboxylic acidHCID 22309456(6-Methoxypyridin-3-yl)boronic acid--hydrogen chloride (1/1)

Product 1

HCID 20526395-(6-Methoxy-3-pyridinyl)-2-thiophenecarboxylic acid

Procedure

The title compound is prepared as described in EXAMPLE 31, Part I, but with 5-bromothiophene-2-carboxylic acid and 6-methoxypyridin-3-ylboronic acid hydrochloride as starting materials, and 10 molar equivalents of 0.4M aqueous sodium carbonate. 1H NMR (DMSO) δ 13.10 (br s, 1H), 8.55 (d, 1H), 8.03 (dd, 1H), 7.66 (d, 1H), 7.50 (d, 1H), 6.90 (d, 1H). ESI MS (M+1)+: 236.

Sources & evidence

ORD record
ord-349b88eaaed04fd88209b2451775f29e
Source dataset
uspto-grants-2011_05
Patent number
US07947684B2

Reaction notes

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