3-formyl-N-methyl-1H-indole-2-carboxamide → N-methyl-3-vinyl-1H-indole-2-carboxamide

HRID 1362432Notes

Reaction equation

[CH2:1]([Li])CCC.[CH:6]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]=1[C:17]([NH:19][CH3:20])=[O:18])=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH3:20][NH:19][C:17]([C:9]1[NH:10][C:11]2[C:16]([C:8]=1[CH:6]=[CH2:1])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:18]

Participants

Conditions

Temperature: 0 °C

Procedure

n-Butyllithium (2.5M in hexanes) (48.6 mL, 121.7 mmol) was added dropwise to an ice-cooled solution of methyl triphenylphosphoniumbromide (43.5 g, 121.7 mmol) in THF (500 mL). The mixture was stirred at 0° C. for 1 h then at rt for 2 h. 3-Formyl-N-methyl-1H-indole-2-carboxamide (1.96 g, 9.7 mmol) in THF (100 mL) was added and the mixture stirred at rt for 2 h. The solvent was evaporated and the residue dissolved in ethyl acetate and washed twice with water. The organic phase was dried over magnesium bromide and evaporated in vacuo. The crude mixture was chromatographed over silica gel eluting with 40% ethyl acetate in hexanes to afford the title compound (730 mg (38%). 1H NMR (300 MHz, DMSO-d6) δ 11.48 (s, 1H), 8.04 (s, 1H), 7.92 (d, J=8.0 Hz, 1H), 7.42 (d, J=7.9 Hz, 1H), 7.33 (d, J=18 Hz, 1H), 7.22 (t, J=7.6 Hz, 1H), 7.09 (t, J=7.2 Hz, 1H), 5.77 (d, J=18.4 Hz, 1H), 5.27 (d, J=11.6 Hz, 1H), 2.81 (s, 3H).

Workup

waitat rt for 2 h
stirringthe mixture stirred at rt for 2 h
customThe solvent was evaporated
dissolutionthe residue dissolved in ethyl acetate
washwashed twice with water
dry with materialThe organic phase was dried over magnesium bromide
customevaporated in vacuo
customThe crude mixture was chromatographed over silica gel eluting with 40% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-bf6c3458b0d241eea6965562d02d7568
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879872B2

Reaction notes

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