Pyridine → tert-butyl 4-(3-bromo-1-(pyridin-4-yl)-1H-indol-6-yl)piperazine-1-carboxylate

HRID 240836Notes

Reaction equation

[Br:1]N1C(=O)CCC1=O.[N:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([N:24]4[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]4)[CH:22]=3)[CH:17]=[CH:16]2)=[CH:11][CH:10]=1.N1C=CC=CC=1>C1COCC1>[Br:1][C:17]1[C:18]2[C:23](=[CH:22][C:21]([N:24]3[CH2:25][CH2:26][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:28][CH2:29]3)=[CH:20][CH:19]=2)[N:15]([C:12]2[CH:11]=[CH:10][N:9]=[CH:14][CH:13]=2)[CH:16]=1

Participants

Conditions

Temperature: -78 °C

Procedure

N-Bromosuccinimide (64.4 mg, 0.36 mmol) was added to a mixture solution of tert-butyl 4-(1-(pyridin-4-yl)-1H-indol-6-yl)piperazine-1-carboxylate (137 mg, 0.36 mmol) in THF (12 mL) 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 (88 μL, 1.09 mmol) was added. After filtering using a diatomite pad, the solution was adsorbed by adding silica gel. Purification by chromatography (silica gel, EA:Hx=4:1) yielded the target compound (49.1 mg, 30%) as white solid.

Workup

stirringthe mixture was further stirred at 0° C. for 1 hour
filtrationAfter filtering
additionby adding silica gel
customPurification by chromatography (silica gel, EA:Hx=4:1)

Sources & evidence

ORD record: ord-05b03a6436fe4d37bebe1438348f766e
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648089B2

Reaction notes

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