Dimethylformamide → HCID 86649376, compound

Reaction equation

[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:14]([C:15]2[S:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:21]=3)=[CH:18][CH:19]=2)=[CH:13][C:12]([CH2:30][OH:31])=[N:11]1.Br.Br[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=1.CN(C=[O:45])C>>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:14]([C:15]2[S:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([S:26]([CH3:29])(=[O:27])=[O:28])[CH:21]=3)=[CH:18][CH:19]=2)=[CH:13][C:12]([CH2:30][O:31][O:45][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=2)=[N:11]1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 24758Sodium hydride

HCID 27347202-(Bromomethyl)pyridine hydrobromide

HCID 59632050HCID 59632050, compound

Product 1

HCID 86649376HCID 86649376, compoundYield 67%

Procedure

NaH (60% in mineral oil, 90 mg, 2.25 mmol) was added at 0° C. to a stirred mixture of [1-(2-chlorophenyl)-5-{5-[3-(methylsulfonyl)phenyl]-2-thienyl}-1H-pyrazol-3-yl]methanol (222 mg, 0.5 mmol), 2-(bromomethyl)pyridine hydrobromide (190 mg, 0.75 mmol), and anhydrous DMF (5 mL) under N2, the resulting mixture was stirred at it for 4 h. The reaction mixture was poured into ice-water, and extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4, and evaporated in vacuo. The crude product was purified by flash chromatography (0-100% EtOAc/hexanes) to give the title compound as a colorless semi-solid (179 mg, 67%). 1HNMR (CDCl3): δ 8.58 (m, 1H), 8.04 (m, 1H), 7.82 (m, 1H), 7.74-7.71 (m, 2H), 7.57-7.44 (m, 6H), 7.20 (m, 2H), 6.76 (m, 2H), 4.78 (m, 4H), 3.08 (s, 3H). MS(ES): 536 [M+H]+.