HCID 16116080, compound → HCID 16114654, compound

HRID 1008633Notes

Reaction equation

HRID 1008633 reaction equation
[CH:1]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[C:22]#[C:23][CH2:24][CH2:25][OH:26])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CN(C=O)C>[CH:1]([N:14]1[C:15]2[C:16](=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[CH:22]=[C:23]1[CH2:24][CH2:25][OH:26])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 16116080HCID 16116080, compound

Product 1

HCID 16114654HCID 16114654, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the crude 4-[2-(benzhydryl-amino)-5-chloro-phenyl]-but-3-yn-1-ol (25.5 g) and Cul (2.7 g, 14.1 mmol) in DMF (200 mL) was heated at 125° C. for 24 hours. The reaction mixture was filtered through celite and rinsed with EtOAc. The filtrate was concentrated, redissolved in EtOAc, washed with water (3×) and brine, and dried over MgSO4. Silica gel column chromatography (30% EtOAc/hexanes) yielded the desired 2-(1-Benzhydryl-5-chloro-1H-indol-2-yl)-ethanol as a yellow solid (14.5 g, 73% over 2 steps).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washrinsed with EtOAc
  3. concentrationThe filtrate was concentrated
  4. dissolutionredissolved in EtOAc
  5. washwashed with water (3×) and brine
  6. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-15ef1552353b4e36a1a8e56fa7434c8e
Source dataset
uspto-grants-2004_09
Patent number
US06797708B2

Reaction notes

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