Ethyl 3-bromo-1-(3-(naphthalen-1-yloxy)propyl)-1h-indole-2-carboxylate → Ethyl 3-benzyl-1-(3-(naphthalen-1-yloxy)propyl)-1h-indole-2-carboxylate

HRID 533245Notes

Reaction equation

HRID 533245 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][CH2:12][CH2:13][O:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[C:3]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26].[Br-].[CH2:31]([Zn+])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1COCC1.C(OCC)(=O)C>[CH2:31]([C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][CH2:12][CH2:13][O:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[C:3]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 2

HCID 67316935Ethyl 3-bromo-1-(3-(naphthalen-1-yloxy)propyl)-1h-indole-2-carboxylateHCID 178419772HCID 178419772, compound

Product 1

HCID 67316098Ethyl 3-benzyl-1-(3-(naphthalen-1-yloxy)propyl)-1h-indole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of EXAMPLE 31C (100 mg), 0.5M benzyl zinc(II) bromide in THF (1.32 mL) and (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium(II) (18 mg) in THF (2 mL) was stirred at 60° C. for 16 hours. The mixture was diluted with ethyl acetate, and the organic phase was washed with water and brine and dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash chromatography on silica gel with 0-8% ethyl acetate/hexanes.

Workup

  1. washthe organic phase was washed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash chromatography on silica gel with 0-8% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-ba0ab7c9df734c92bd7332df7cf1cb29
Source dataset
uspto-grants-2014_10
Patent number
US08853209B2

Reaction notes

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