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

HRID 2174050노트

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HRID 2174050 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1d57d63e06574e7097ed9a5a38162cb4
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056874B2

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