Toluene → 5-Methyl-1-tosyl-7-vinyl-1H-indole-4-carbaldehyde

HRID 2174050ノート

反応式

HRID 2174050 の反応式
[CH3:1][C:2]1[C:3](NC(=O)OC(C)(C)C)=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:6]=[CH:5]2.[C:29]([O-:32])([O-])=O.[K+].[K+].[C:35]1(C)C=CC=C[CH:36]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>CCOC(C)=O>[CH3:1][C:2]1[CH:10]=[C:9]([CH:35]=[CH2:36])[C:8]2[N:7]([S:11]([C:14]3[CH:15]=[CH:16][C:17]([CH3:18])=[CH:19][CH:20]=3)(=[O:12])=[O:13])[CH:6]=[CH:5][C:4]=2[C:3]=1[CH:29]=[O:32]

参加物

6

反応物 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 86701666tert-Butyl (5-methyl-1-tosyl-1H-indol-4-yl)carbamate

生成物 1

HCID 721921455-Methyl-1-tosyl-7-vinyl-1H-indole-4-carbaldehyde

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To a suspension of 7-chloro-5-methyl-1-tosyl-1H-indole-4-carbaldehyde (Example 110-E) (73 mg, 0.210 mmol) and vinylboronic anhydride pyridine complex (152 mg, 0.630 mmol) and K2CO3 (290 mg, 2.09 mmol) in toluene (1.7 mL) water (0.7 mL) Pd(OAc)2 (4.71 mg, 0.021 mmol) and S-Phos (CAS#657408-07-6) (17.2 mg, 0.042 mmol) were added, and the reaction was stirred at 80° C. After 1 hour the reaction was diluted with EtOAc. The organics were washed with water, dried over MgSO4, filtered and concentrated. The mixture was loaded onto silica gel and purified by flash chromatography (0-40% EtOAc in heptanes) to the title compound. MS (ESI+) m/z 340.1 (M+H).

後処理

  1. additionwere added
  2. washThe organics were washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography (0-40% EtOAc in heptanes) to the title compound

出典と根拠

ORDレコード
ord-1d57d63e06574e7097ed9a5a38162cb4
出典データセット
uspto-grants-2015_06
特許番号
US09056874B2

反応ノート

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