Sodium hydride → HCID 57908494, compound

HRID 2426986Notes

Reaction equation

HRID 2426986 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([O:12][CH3:13])=[O:11])[CH:3]=[CH:2]1.Br[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=1.[H-].[Na+]>CN(C=O)C>[F:23][C:22]([F:24])([F:25])[C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[CH2:15][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([O:12][CH3:13])=[O:11])[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 676694Methyl indole-7-carboxylate

Product 1

HCID 57908494HCID 57908494, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 1H-indole-7-carboxylate (1 g, 5.71 mmol) and 1-(bromomethyl)-3-(trifluoromethyl)benzene (956 ul, 6.28 mmol) were dissolved in DMF (16 ml), in an ice bath. 60% w/w NaH (251 mg, 6.28 mmol) was added portionwise. The ice bath was removed and the mixture stirred at RT for 30 min. The reaction mixture was quenched with NH4Cl(sat.) and extracted 3 times with ether. The organic layers were combined, washed with water and brine. The compound was purified by flash chromatography on silica gel. 1H NMR (500 MHz, DMSO-d6): δ 7.40 (d, 1H), 7.25 (s, 1H), 7.10 (m, 1H), 7.00 (m, 2H), 6.75 (s, 1H), 6.65 (t, 1H), 6.50 (d, 1H), 6.25 (s, 1H), 5.25 (s, 2H), 2.05 (d, 3H).

Workup

  1. customThe ice bath was removed
  2. customThe reaction mixture was quenched with NH4Cl(sat.)
  3. extractionextracted 3 times with ether
  4. washwashed with water and brine
  5. customThe compound was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-e055d55e362e4547a75727fd0629e3b3
Source dataset
uspto-grants-2011_06
Patent number
US07968578B2

Reaction notes

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