Bromide ion → HCID 21468933, compound

HRID 1938609Notes

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 mmoles, 1.1 g) in 100 ml THF and stirred at 0° C. for 30 minutes. Methyl 3-bromononanoate (5.6 mmoles, 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-36b84adf07c44c14bf6f2811e2aa332b
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05693633

Reaction notes

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