Acetone → HCID 59632050, compound

HRID 2369053Notes

Reaction equation

HRID 2369053 reaction equation
[Li+].[BH4-].C[O:4][C:5]([C:7]1[CH:11]=[C:10]([C:12]2[S:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:18]=3)=[CH:15][CH:16]=2)[N:9]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:33])[N:8]=1)=O.CC(C)=O.O>C1COCC1>[Cl:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[N:9]1[C:10]([C:12]2[S:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([S:23]([CH3:26])(=[O:24])=[O:25])[CH:18]=3)=[CH:15][CH:16]=2)=[CH:11][C:7]([CH2:5][OH:4])=[N:8]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 4148881Lithium borohydrideHCID 59631939HCID 59631939, compound

Product 1

HCID 59632050HCID 59632050, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiBH4 (1.0M in THF, 14 mL, 28 mmol) was added dropwise at rt to a stirred solution of 1-(2-chloro-phenyl)-5-[5-(3-methanesulfonyl-phenyl)-thiophen-2-yl]-1H-pyrazole-3-carboxylic acid methyl ester (4.38 g, 9.26 mmol) in anhydrous THF (100 mL) under N2, and the resulting mixture was stirred at rt for 3d. Acetone (2 mL) and water (2 mL) was added successively at 0° C. and the solid was filtered off. The filtrate was concentrated in vacuo. The residue was taken up in EtOAc (200 mL), washed with water and brine, dried over Na2SO4 and evaporated in vacuo. The crude product was purified by flash chromatography (0-90% EtOAc/hexanes) to give the title compound as a white solid (3.1 g, 75%). 1HNMR (CDCl3): δ 8.04 (m, 1H), 7.84-7.81 (m, 1H), 7.74-7.72 (m, 1H), 7.58-7.44 (m, 5H), 7.21 (d, 1H), 6.76 (d, 1H), 6.69 (s, 1H), 4.80 (s, 2H), 3.07 (s, 3H), 1.65 (brs, 1H). MS(ES): 445 [M+H]+.

Workup

  1. filtrationthe solid was filtered off
  2. concentrationThe filtrate was concentrated in vacuo
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo
  6. customThe crude product was purified by flash chromatography (0-90% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b50733aef2244f3dbe14fe17f50d742f
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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