反応式
[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]=1参加物
実験手順
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.
後処理
- customMeOH was removed in vacuo
- washwashed with sat. aq. NaHCO3 (100 mL)
- dry with materialdried over Na2SO4
- concentrationThe reaction was concentrated in vacuo
- customThe resulting crude product was purified by column chromatography
出典と根拠
- ORDレコード
- ord-79f24434c5fd493c98a3bf0fc310f1ad
- 出典データセット
- uspto-grants-2011_07
- 特許番号
- US07977368B2
関連ノート
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