Water → HCID 50991463, compound

HRID 2192247Notes

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-a9a7879b337c4f608e1b0ae98082c994
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329708B2

Reaction notes

Loading…