Sodium Bicarbonate → HCID 59252823, compound

HRID 563384Notes

Reaction equation

O[CH:2]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]([N:14]([CH3:16])[CH3:15])=[O:13])[CH:7]=[CH:6]2.[CH3:23][O:24][C:25]([O:29][Si](C)(C)C)=[C:26]([CH3:28])[CH3:27].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:15][N:14]([CH3:16])[C:12]([N:8]1[C:9]2[C:5](=[CH:4][C:3]([CH:2]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:26]([CH3:28])([CH3:27])[C:25]([O:24][CH3:23])=[O:29])=[CH:11][CH:10]=2)[CH:6]=[CH:7]1)=[O:13]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 5-(hydroxy(phenyl)methyl)-N,N-dimethyl-1H-indole-1-carboxamide (0.72 g, 2.5 mmol) and (1-methoxy-2-methylprop-1-enyloxy)trimethylsilane (8 mL) in anhydrous dichloromethane (6 mL) was added boron trifluoride diethyl ether complex (0.83 mL, 6.6 mmol) dropwise at 0° C. under argon. After stirring at 0° C. for 30 min and rt for 3.5 hr, the mixture was poured into a saturated aqueous sodium bicarbonate solution maintained at 0° C. The reaction mixture was stirred well, extracted with ethyl acetate (20 mL), dried (Na2SO4) and concentrated. Silica gel flash chromatography gave methyl 3-(1-(dimethylcarbamoyl)-1H-indol-5-yl)-2,2-dimethyl-3-phenylpropanoate (0.9 g, 2.4 mmol, 96% yield) as a glassy solid, the NMR spectrum of which was consistent with the desired structure.

Workup

temperaturemaintained at 0° C
stirringThe reaction mixture was stirred well
extractionextracted with ethyl acetate (20 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-eb937e6d454e4f7d8f4c8ac411c21e6d
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067447B2

Reaction notes

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