Dimethylformamide → HCID 86649376, compound

HRID 2369064Notes

Reaction equation

HRID 2369064 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

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 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]+.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. customThe crude product was purified by flash chromatography (0-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-09ca648e38cf484e9d4c446197806877
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

Loading…