Dimethylamine → (5-dimethylaminomethyl-2-trifluoromethyl-1H-indol-3-yl)-acetic acid ethyl ester

HRID 216681Notes

Reaction equation

HRID 216681 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:15]Br)[CH:13]=2)[N:8](C(=O)C)[C:7]=1[C:20]([F:23])([F:22])[F:21])[CH3:2].[CH3:25][NH:26][CH3:27]>C1COCC1.C(O)C>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:15][N:26]([CH3:27])[CH3:25])[CH:13]=2)[NH:8][C:7]=1[C:20]([F:23])([F:22])[F:21])[CH3:2]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 59192044(1-acetyl-5-bromomethyl-2-trifluoromethyl-1H-indol-3-yl)-acetic acid ethyl ester

Product 1

HCID 59192019(5-dimethylaminomethyl-2-trifluoromethyl-1H-indol-3-yl)-acetic acid ethyl esterYield 99%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1-acetyl-5-bromomethyl-2-trifluoromethyl-1H-indol-3-yl)-acetic acid ethyl ester (378 mg, 0.93 mmol) in THF (16.0 mL) is added a 33% solution of dimethylamine in ethanol (8.0 mL). The resulting reaction mixture is stirred for 15 h at room temperature, followed by removal of the volatiles in vacuo. The residue is purified by flash column chromatography (silica gel, CH2Cl2/MeOH 9:1) to afford the title compound as a yellow solid (303 mg, 0.92 mmol, 99%). 1H NMR (400 MHz, CDCl3, 298 K): δ=12.31 (s, 1H), 7.71 (s, 1H), 7.59 (d, J=8.6 Hz, 1H), 7.42 (d, J=8.6 Hz, 1H), 4.15 (q, J=7.1 Hz, 2H), 4.11 (s, 2H), 3.90 (s, 2H), 2.64 (s, 6H), 1.24 (t, J=7.1 Hz, 3H). MS (ES+): 329 (M(C16H19F3N2O2)+H)+.

Workup

  1. customThe resulting reaction mixture
  2. customfollowed by removal of the volatiles in vacuo
  3. customThe residue is purified by flash column chromatography (silica gel, CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-1e7f486d30ca448daaae8221fb0f36bd
Source dataset
uspto-grants-2012_06
Patent number
US08193236B2

Reaction notes

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