Sodium hydride → HCID 59657511, compound

HRID 2055549Notes

Reaction equation

HRID 2055549 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]([N:14]3[CH2:19][CH2:18][C:17]4([C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[CH2:21][O:20]4)[CH2:16][CH2:15]3)=[O:13])=[C:7]([CH3:11])[NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[F:30][C:31]([F:45])([F:44])[C:32]1[CH:33]=[C:34]([CH:37]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:39]=1)[CH2:35]Br>CN(C)C=O>[F:30][C:31]([F:44])([F:45])[C:32]1[CH:33]=[C:34]([CH:37]=[C:38]([C:40]([F:43])([F:41])[F:42])[CH:39]=1)[CH2:35][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=2)[C:6]([C:12]([N:14]2[CH2:15][CH2:16][C:17]3([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[CH2:21][O:20]3)[CH2:18][CH2:19]2)=[O:13])=[C:7]1[CH3:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1225733,5-Bis(trifluoromethyl)benzyl bromideHCID 59657535HCID 59657535, compound

Product 1

HCID 59657511HCID 59657511, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.031 g (0.080 mmol) 1′-[(6-chloro-2-methyl-1H-indol-3-yl)carbonyl]-3H-spiro[2-benzofuran-1,4′-piperidine] (5) in 1 ml dry N,N-dimethylformamide were added 0.004 g (0.08 mmol) sodium hydride (50% in oil). After stirring for 20 min 0.015 ml (0.08 mmol) 3,5-bis(trifluoromethyl)benzyl bromide were added. After stirring for 16 h the reaction mixture was quenched with water and extracted with ethyl acetate (2×50 ml). The combined organic layers were washed with water (2×30 ml) and brine (1×30), dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (n-heptane/ethyl acetate) to give the title compound (0.020 g; 41%) as a white solid. MS m/e (%): 607 (M+H+, 100).

Workup

  1. additionwere added
  2. customwas quenched with water
  3. extractionextracted with ethyl acetate (2×50 ml)
  4. washThe combined organic layers were washed with water (2×30 ml) and brine (1×30)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (n-heptane/ethyl acetate)

Sources & evidence

ORD record
ord-5be5cd41dcc041bcb2e9342d403a38a5
Source dataset
uspto-grants-2008_02
Patent number
US07332501B2

Reaction notes

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