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Water → 5,7-Dimethyl-1-tosyl-3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)-1H-indole-4-carbaldehyde

HRID 2174070
ノート
印刷プレビュー

反応式

HRID 2174070 の反応式
Br[C:2]1[C:10]2[C:9]([CH:11]=[O:12])=[C:8]([CH3:13])[CH:7]=[C:6]([CH3:14])[C:5]=2[N:4]([S:15]([C:18]2[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH:3]=1.[CH3:25][Si:26]([CH3:46])([CH3:45])[CH2:27][CH2:28][O:29][CH2:30][N:31]1[C:35](B2OC(C)(C)C(C)(C)O2)=[CH:34][CH:33]=[N:32]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>COCCOC.C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:13][C:8]1[CH:7]=[C:6]([CH3:14])[C:5]2[N:4]([S:15]([C:18]3[CH:19]=[CH:20][C:21]([CH3:22])=[CH:23][CH:24]=3)(=[O:17])=[O:16])[CH:3]=[C:2]([C:35]3[N:31]([CH2:30][O:29][CH2:28][CH2:27][Si:26]([CH3:46])([CH3:45])[CH3:25])[N:32]=[CH:33][CH:34]=3)[C:10]=2[C:9]=1[CH:11]=[O:12]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 447552015-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazoleHCID 867016993-Bromo-5,7-dimethyl-1-tosyl-1H-indole-4-carbaldehyde

生成物 1

HCID 898859785,7-Dimethyl-1-tosyl-3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)-1H-indole-4-carbaldehyde

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 6344Dichloromethane溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

To a suspension of 3-bromo-5,7-dimethyl-1-tosyl-1H-indole-4-carbaldehyde (100 mg, 0.246 mmol), 1-(2-trimethylsilylethoxy)methyl-1H-pyrazole-5-boronic acid pinacol ester (CAS #: 903550-12-9) (239 mg, 0.738 mmol), and K3PO4 (157 mg, 0.738 mmol) in DME (1 mL)/H2O (0.5 mL) was added Pd(PPh3)4 (56.9 mg, 0.049 mmol), and then the mixture was stirred at 80° C. for 16 h. The reaction mixture was cooled down to room temperature. The mixture was diluted with CH2Cl2. The bi-phase layer was partitioned. The organic layer was separated, dried over MgSO4, filtered and concentrated. The resulting residue was purified by silica gel flash column chromatography [heptane/(30% EtOAc in CH2Cl2)=1/0 to 4/6] to give the title compound. MS (ESI+) m/z 524.2 (M+H).

後処理

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. customThe bi-phase layer was partitioned
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by silica gel flash column chromatography [heptane/(30% EtOAc in CH2Cl2)=1/0 to 4/6]

出典と根拠

ORDレコード
ord-8a1fc11931864dcfbc150b599200a9d1
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09056874B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート