Water → 5-Chloro-N-{2-ethyl-1-[1-(4-hydroxybenzyl)-1H-pyrazol-5-yl]butyl}thiophene-2-sulfonamide

HRID 748042Notes

Reaction equation

HRID 748042 reaction equation
[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][CH:11]([C:17]2[N:21]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29]C)=[CH:25][CH:24]=3)[N:20]=[CH:19][CH:18]=2)[CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])(=[O:9])=[O:8])=[CH:4][CH:3]=1.B(Br)(Br)Br.O>C(Cl)Cl>[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][CH:11]([C:17]2[N:21]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=3)[N:20]=[CH:19][CH:18]=2)[CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])(=[O:8])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 112599035-Chloro-N-{2-ethyl-1-[1-(4-methoxybenzyl)-1H-pyrazol-5-yl]butyl}thiophene-2-sulfonamide

Product 1

HCID 112709615-Chloro-N-{2-ethyl-1-[1-(4-hydroxybenzyl)-1H-pyrazol-5-yl]butyl}thiophene-2-sulfonamideYield 72.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5-chloro-N-{2-ethyl-1-[1-(4-methoxybenzyl)-1H-pyrazol-5-yl]butyl}thiophene-2-sulfonamide (57.0 mg, 0.121 mmol) in CH2Cl2 (3 mL) at −78° C. was added a solution of boron tribromide (1 M in CH2Cl2, 0.40 mL, 0.40 mmol) dropwise. The reaction mixture was warmed to room temperature gradually over several hours and allowed to stir overnight. Water (10 mL) was added slowly to the mixture. It was then extracted with EtOAc (3×20 mL), dried (Na2SO4) and concentrated. Column chromatography (EtOAc/hex, 3:7) provided 40 mg (72%) of 5-chloro-N-{2-ethyl-1-[1-(4-hydroxybenzyl)-1H-pyrazol-5-yl]butyl}thiophene-2-sulfonamide as a white solid (mp=90-92° C.).

Workup

  1. extractionIt was then extracted with EtOAc (3×20 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3042460af94f4959931b07b4b6f84fe8
Source dataset
uspto-grants-2008_07
Patent number
US07399778B2

Reaction notes

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