Bromide ion → HCID 21468933, compound

HRID 866259Notes

Reaction equation

C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[CH:22]2)#[N:12].Br[CH:29]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:30][C:31]([O:33][CH3:34])=[O:32].[Br-]>C1COCC1>[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([CH:29]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:23]=[CH:22]2)#[N:12]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium bis(trimethylsilyl)amide (5.6 ml of 1M solution in THF) in 40 ml THF was added dropwise at 0° C. to a solution of 5-(2-cyanophenyl)indole (5.04 moles, 1.1 g) in 100 ml THF and stirred at 0° C. for 30 minutes. Methyl 3-bromononanoate (5.6 moles, 1.32 g) in 20 ml THF was added dropwise. The reaction was stirred at room temperature for 12 hours. An additional 5 mmoles of the base and the bromide were added. The reaction was stirred an additional 12 hours, added to ice water and extracted into ethyl acetate. The organic phase was dried over sodium sulfate and concentrated. The intermediate was chromatographed over silica gel eluted with 50% ether in hexane to yield 700 mg of methyl 3-[5-(2-cyanophenyl)indol-1-yl]nonanoate.

Workup

stirringThe reaction was stirred at room temperature for 12 hours
stirringThe reaction was stirred an additional 12 hours
extractionextracted into ethyl acetate
dry with materialThe organic phase was dried over sodium sulfate
concentrationconcentrated
customThe intermediate was chromatographed over silica gel
washeluted with 50% ether in hexane

Sources & evidence

ORD record: ord-b80cb55dd4be4a769db7aa099caa3b56
Source dataset: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05569768

Reaction notes

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