Water → N-((3-iodo-1-(methoxymethyl)-1H-pyrazol-4-yl)methyl)-4-(trifluoromethyl)benzene-sulfonamide

HRID 1011617

반응식

HRID 1011617 반응식
[I:1][C:2]1[C:6]([CH:7]=[N:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:5][N:4]([CH2:22][O:23][CH3:24])[N:3]=1.[BH4-].[Na+].O>CO>[I:1][C:2]1[C:6]([CH2:7][NH:8][S:9]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:16][CH:17]=2)(=[O:10])=[O:11])=[CH:5][N:4]([CH2:22][O:23][CH3:24])[N:3]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 67313312N-((3-iodo-1-(methoxymethyl)-1H-pyrazol-4-yl)methylene)-4-(trifluoromethyl)benzenesulfonamide

생성물 1

HCID 57659754N-((3-iodo-1-(methoxymethyl)-1H-pyrazol-4-yl)methyl)-4-(trifluoromethyl)benzene-sulfonamide수율 37%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

N-((3-Iodo-1-(methoxymethyl)-1H-pyrazol-4-yl)methylene)-4-(trifluoromethyl)benzenesulfonamide (41) (7.41 g, 15.66 mmol) was suspended in MeOH (20 mL). NaBH4 was added portionwise and the reaction was stirred for 3 hr until TLC monitoring revealed the disappearance of starting material. Water (20 mL) was added and MeOH was removed in vacuo. The residue was taken up in EtOAc (100 mL) and washed with sat. aq. NaHCO3 (100 mL) and dried over Na2SO4. The reaction was concentrated in vacuo. The resulting crude product was purified by column chromatography using EtOAc/hexane gradients to yield N-((3-iodo-1-(methoxymethyl)-1H-pyrazol-4-yl)methyl)-4-(trifluoromethyl)benzenesulfonamide (42) (1.44 g, 37% over two steps) as a clear oil that solidified upon standing.

후처리

  1. customMeOH was removed in vacuo
  2. washwashed with sat. aq. NaHCO3 (100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationThe reaction was concentrated in vacuo
  5. customThe resulting crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-79f24434c5fd493c98a3bf0fc310f1ad
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977368B2

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