Triethylamine → {6-[4-(4-Trifluoromethyl-phenyl)-piperazine-1-sulfonyl]-indol-1-yl}-acetic acid methyl ester

HRID 2110128Notes

Reaction equation

HRID 2110128 reaction equation
[CH3:1][O:2][C:3](=[O:34])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10](Br)=[C:11]([S:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=4)[CH2:19][CH2:18]3)(=[O:16])=[O:15])[CH:12]=2)[CH:7]=[CH:6]1.C(N(CC)CC)C>[Pd].[C]>[CH3:1][O:2][C:3](=[O:34])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([S:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=4)[CH2:19][CH2:18]3)(=[O:15])=[O:16])[CH:12]=2)[CH:7]=[CH:6]1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 57565263HCID 57565263, compound

Product 1

HCID 57565246{6-[4-(4-Trifluoromethyl-phenyl)-piperazine-1-sulfonyl]-indol-1-yl}-acetic acid methyl esterYield 83.1%

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

{5-Bromo-6-[4-(4-trifluoromethyl-phenyl)-piperazine-1-sulfonyl]-indol-1-yl}-acetic acid methyl ester (135 mg, 0.24 mmol), triethylamine (40 μL, 0.29 mmol) and 10% Pd/carbon (cat) were stirred under an atmosphere of hydrogen until all the starting material was gone. The reaction was then filtered through celite, concentrated and purified by flash column chromatography (60% hexanes in ethyl acetate) to afford {6-[4-(4-trifluoromethyl-phenyl)-piperazine-1-sulfonyl]-indol-1-yl}-acetic acid methyl ester (96 mg, 83%) as a clear oil. 1H NMR (400 MHz, CDCl3) δ 7.76(d, 1H) 7.75 (d, 1H), 7.51 (dd, 1H), 7.44 (dd, 2H), 7.31 (d, 1H), 6.84 (d, 2H), 6.67 (d, 1H), 4.11 (dd, 2H), 3.78 (s, 3H), 3.33 (m, 4H), 3.16 (m, 4H).

Workup

  1. filtrationThe reaction was then filtered through celite,
  2. concentrationconcentrated
  3. custompurified by flash column chromatography (60% hexanes in ethyl acetate)

Sources & evidence

ORD record
ord-d733aac41c35455ea5ca492b3e78ecff
Source dataset
uspto-grants-2009_04
Patent number
US07517884B2

Reaction notes

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