Sodium hydride → HCID 68545394, compound

HRID 2243164Notes

Reaction equation

HRID 2243164 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-a068b9fee09041b3947db8270eccdf66
Source dataset
uspto-grants-2010_03
Patent number
US07674818B2

Reaction notes

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