Sodium hydride → HCID 68545394, compound

HRID 854501Notes

Reaction equation

HRID 854501 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH:17]=[CH:16]3)=[CH:6][CH:5]=1.[F:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=1>C1COCC1>[F:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][N:18]2[C:19]3[C:15](=[CH:14][C:13]([O:12][CH2:11][CH2:10][C:7]4[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=4)=[CH:21][CH:20]=3)[CH:16]=[CH:17]2)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 68552474HCID 68552474, compound

Product 1

HCID 68545394HCID 68545394, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 0.2 g of a 60% dispersion of NaH in mineral oil, suspended in 20 ml of anhydrous THF, was added 0.61 g (2.38 mmol) 5-[2-(4-fluoro-phenyl)-ethoxy]-1H-indole from Step 1. The slurry was stirred for 15 min upon which time 0.33 ml (2.6 mmol) 4-fluorobenzylbromide was added. The slurry was stirred overnight. The slurry was concentrated under vacuum and the residue was redissolved in ethyl acetate and washed with brine. The organic phase was dried over MgSO4 and concentrated. The residue was chromatographed on silica to afford 0.61 g 1-(4-fluoro-benzyl)-5-[2-(4-fluoro-phenyl)-ethoxy]-1H-indole as a fluffy powder.

Workup

  1. additionwas added
  2. concentrationThe slurry was concentrated under vacuum
  3. dissolutionthe residue was redissolved in ethyl acetate
  4. washwashed with brine
  5. dry with materialThe organic phase was dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-2beb0fadcc6f4ff3a2d4f5e18a82755c
Source dataset
uspto-grants-2007_08
Patent number
US07259182B2

Reaction notes

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