Sodium hydride → N-[9-(3-Fluorobenzyl)-6-bromo-2,3,4,9-tetrahydro-1H-carbazol-3-yl]isobutyramide

HRID 545501Notes

Reaction equation

HRID 545501 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH:7]([NH:15][C:16](=[O:20])[CH:17]([CH3:19])[CH3:18])[CH2:6][C:5]2=1.[H-].[Na+].[F:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27]Br>CN(C=O)C.O>[F:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27][N:11]1[C:10]2[CH2:9][CH2:8][CH:7]([NH:15][C:16](=[O:20])[CH:17]([CH3:18])[CH3:19])[CH2:6][C:5]=2[C:4]2[C:12]1=[CH:13][CH:14]=[C:2]([Br:1])[CH:3]=2

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 680073-Fluorobenzyl bromideHCID 46098126HCID 46098126, compound

Product 1

HCID 57431656N-[9-(3-Fluorobenzyl)-6-bromo-2,3,4,9-tetrahydro-1H-carbazol-3-yl]isobutyramideYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Add N-(6-bromo -2,3,4,9-tetrahydro-1H-carbazol-3-yl)isobutyramide (0.25 g, 0.75 mmol) to a suspension of sodium hydride (0.036 g, 0.90 mmol of a 60% dispersion in mineral oil) in DMF (3 mL) and stir for 15 min. Add 3-fluorobenzylbromide (0.10 mL, 0.90 mmol) and stir for 18-72 h. Dilute with water and collect the precipitate by filtration. Purify by silica gel chromatography eluting with 20-100% EtOAc/hexanes gradient to give 0.23 g of a white solid (71%). MS (ES): m/z 443 (M+1), 445 (M+H+2); HPLC: Rt=3.71 min (97.1%); m.p.=177-179° C.

Workup

  1. customcollect the precipitate
  2. filtrationby filtration
  3. customPurify by silica gel chromatography
  4. washeluting with 20-100% EtOAc/hexanes gradient

Sources & evidence

ORD record
ord-cc37a47bb25349058f5a9e56927ade27
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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