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

HRID 2174050Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 80 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-1d57d63e06574e7097ed9a5a38162cb4
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056874B2

Reaction notes

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