Potassium Fluoride → [4-(3-Ethynyl-5-trifluoromethyl-benzenesulfonylamino)-4,5,6,7-tetrahydro-indazol-1-yl]-acetic acid ethyl ester

HRID 1645169ノート

反応式

HRID 1645169 の反応式
[CH2:1]([O:3][C:4](=[O:35])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][CH:10]([NH:15][S:16]([C:19]3[CH:24]=[C:23]([C:25]#[C:26][Si](C)(C)C)[CH:22]=[C:21]([C:31]([F:34])([F:33])[F:32])[CH:20]=3)(=[O:18])=[O:17])[C:9]=2[CH:8]=[N:7]1)[CH3:2].[F-].[K+]>CN(C)C=O.O>[CH2:1]([O:3][C:4](=[O:35])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][CH:10]([NH:15][S:16]([C:19]3[CH:20]=[C:21]([C:31]([F:33])([F:34])[F:32])[CH:22]=[C:23]([C:25]#[CH:26])[CH:24]=3)(=[O:18])=[O:17])[C:9]=2[CH:8]=[N:7]1)[CH3:2]

参加物

5

反応物 2

HCID 522689Potassium FluorideHCID 59152887[4-(3-Trifluoromethyl-5-trimethylsilanylethynyl-benzenesulfonylamino)-4,5,6,7-tetrahydro-indazol-1-yl]-acetic acid ethyl ester

生成物 1

HCID 59152882[4-(3-Ethynyl-5-trifluoromethyl-benzenesulfonylamino)-4,5,6,7-tetrahydro-indazol-1-yl]-acetic acid ethyl ester収率 98.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of [4-(3-trifluoromethyl-5-trimethylsilanylethynyl-benzenesulfonylamino)-4,5,6,7-tetrahydro-indazol-1-yl]-acetic acid ethyl ester (40.0 mg, 0.076 mmol) in N,N-dimethylformamide and water (3 mL, 150:1) was added potassium fluoride (23.0 mg, 0.30 mmol). The mixture was stirred at room temperature for 4 hours. The resulting mixture was poured into ice and extracted with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified by column chromatography (gradient elution, 0-5% methanol in dichloromethane) to afford [4-(3-ethynyl-5-trifluoromethyl-benzenesulfonylamino)-4,5,6,7-tetrahydro-indazol-1-yl]-acetic acid ethyl ester (34.0 mg, 98.2%) as a white solid. MS calcd. for C20H20F3N3O4S 455, obsd. (ESI+) [(M+H)+] 456.

後処理

  1. additionThe resulting mixture was poured into ice
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified by column chromatography (gradient elution, 0-5% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-376e5853dbf64601b9f76dffadc73f80
出典データセット
uspto-grants-2012_02
特許番号
US08124641B2

反応ノート

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