Water → HCID 50991463, compound

HRID 240838Notes

Reaction equation

[Br:1]N1C(=O)CCC1=O.C([C:13]1[CH:18]=[C:17]([C:19]2[CH:27]=[C:26]3[C:22]([CH:23]=[CH:24][N:25]3[C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)=[CH:21][CH:20]=2)[CH:16]=[CH:15][C:14]=1[OH:34])(C)(C)C.N1C=CC=CC=1.O>C1COCC1>[Br:1][C:23]1[C:22]2[C:26](=[CH:27][C:19]([C:17]3[CH:18]=[CH:13][C:14]([OH:34])=[CH:15][CH:16]=3)=[CH:20][CH:21]=2)[N:25]([C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)[CH:24]=1

Participants

Conditions

Temperature: -78 °C

Procedure

N-Bromosuccinimide (8.1 mg, 0.046 mmol) was added to a mixture solution of tert-butyl 4-(1-(pyridin-4-yl)-1H-indol-6-yl)phenol (10 mg, 0.035 mmol) in THF (0.5 mL) mixture solution at −78° C. After stirring at −78° C. for 2 hours, the mixture was further stirred at 0° C. for 1 hour and then pyridine (8.5 μL, 0.105 mmol) was added. After stirring at room temperature for 30 minutes, water was added and the mixture was extracted with ethyl acetate. The collected organic layer was washed with saturated sodium bicarbonate solution and brine, and then concentrated under reduced pressure by drying with anhydrous magnesium sulfate. The target compound was obtained as white solid.

Workup

stirringthe mixture was further stirred at 0° C. for 1 hour
stirringAfter stirring at room temperature for 30 minutes
extractionthe mixture was extracted with ethyl acetate
washThe collected organic layer was washed with saturated sodium bicarbonate solution and brine
concentrationconcentrated under reduced pressure
dry with materialby drying with anhydrous magnesium sulfate
customThe target compound was obtained as white solid

Sources & evidence

ORD record: ord-1fea495e112f4d1185e4216c0d484772
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648089B2

Reaction notes

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