Sodium hydride → 6-bromo-5-(2-(4-fluorophenyl)allyl)-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 717794Notes

Reaction equation

[H-].[Na+].[Br:3][C:4]1[C:12]2[NH:11][C:10]3[CH2:13][CH2:14][N:15]([CH3:17])[CH2:16][C:9]=3[C:8]=2[CH:7]=[C:6]([CH3:18])[CH:5]=1.Br[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)=[CH2:22]>CN(C=O)C>[Br:3][C:4]1[C:12]2[N:11]([CH2:22][C:21]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)=[CH2:20])[C:10]3[CH2:13][CH2:14][N:15]([CH3:17])[CH2:16][C:9]=3[C:8]=2[CH:7]=[C:6]([CH3:18])[CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (49.8 mg, 21.67 mmol) was charged in DMF (3 mL) and cooled to 0° C. 6-Bromo-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (200 mg, 0.83 mmol) was added and stirred at 0° C. for 5 min. 1-(3-Bromoprop-1-en-2-yl)-4-fluorobenzene (195.25 mg, 0.917 mmol) dissolved in DMF (1 mL) was added at 0° C. and stirred at RT for 2 h. Ice was added and the resultant solid obtained was filtered. The product was purified on silica using 0-7% MeOH:DCM as eluent. Yield: 85 mg.

Workup

additionwas added at 0° C.
stirringstirred at RT for 2 h
additionIce was added
customthe resultant solid obtained
filtrationwas filtered
customThe product was purified on silica using 0-7% MeOH

Sources & evidence

ORD record: ord-d5b30fa914fa4def946cc6dce20a7bcb
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193728B2

Reaction notes

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