Ethyl Acetate → HCID 57565194, compound

HRID 2110127Notes

Reaction equation

HRID 2110127 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([S:15]([C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[NH:23][CH:22]=[CH:21]4)(=[O:17])=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:35]([O:38][CH2:39]C)(=[O:37])[CH3:36]>C(#N)C>[CH3:39][O:38][C:35](=[O:37])[CH2:36][N:23]1[C:24]2[C:20](=[CH:19][C:18]([S:15]([N:12]3[CH2:11][CH2:10][N:9]([C:6]4[CH:7]=[CH:8][C:3]([C:2]([F:27])([F:1])[F:28])=[CH:4][CH:5]=4)[CH2:14][CH2:13]3)(=[O:17])=[O:16])=[CH:26][CH:25]=2)[CH:21]=[CH:22]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 57565259HCID 57565259, compound

Product 1

HCID 57565194HCID 57565194, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-[4-(4-Trifluoromethyl-phenyl)-piperazine-1-sulfonyl]-1H-indole (60 mg, 0.15 mmol), methyl bromo acetate (16 μL, 0.18 mmol) and cesium carbonate (95 mg, 0.29 mmol) were stirred in acetonitrile (10 ml) overnight at 70° C. The reaction mixture was diluted with ethyl acetate, washed with water, brine, dried (Na2SO4) and concentrated to provide {5-[4-(4-trifluoromethyl-phenyl)-piperazine-1-sulfonyl]-indol-1-yl}-acetic acid methyl ester (99%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 8.11(d, 1H) 7.60 (dd, 1H), 7.43 (d, 2H), 7.36 (d, 1H), 7.24 (d, 1H), 6.83 (d, 2H), 6.90 (d, 1H), 4.91 (s, 2H), 3.76 (s, 3H), 3.32-3.30 (m, 4H), 3.15-3.13 (m, 4H).

Workup

  1. washwashed with water, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3fc054770a4d47338a5836d3cf9d63b6
Source dataset
uspto-grants-2009_04
Patent number
US07517884B2

Reaction notes

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