Sodium Carbonate → 2-Fluoro-4-(6-methoxypyridin-3-yl)benzoic acid

HRID 551279Notes

Reaction equation

HRID 551279 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1.Cl.[CH3:13][O:14][C:15]1[N:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>>[F:11][C:4]1[CH:3]=[C:2]([C:18]2[CH:19]=[N:20][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 3026814-Bromo-2-fluorobenzoic acidHCID 22309456(6-Methoxypyridin-3-yl)boronic acid--hydrogen chloride (1/1)

Product 1

HCID 617778962-Fluoro-4-(6-methoxypyridin-3-yl)benzoic acid

Procedure

The title compound is prepared as described in EXAMPLE 31, Part I, but with 4-bromo-2-fluorobenzoic 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 13.30 (br s, 1H), 8.59 (d, 1H), 8.11 (dd, 1H), 7.90 (t, 1H), 7.68-7.57 (m, 2H), 6.91 (d, 1H), 3.88 (s, 3H). ESI MS (M+1)+: 248.

Sources & evidence

ORD record
ord-5b0eb9c0c0804a41b31848cd00fc1cae
Source dataset
uspto-grants-2011_05
Patent number
US07947684B2

Reaction notes

Loading…