Potassium Carbonate → HCID 67442606, compound

HRID 2045241Notes

Reaction equation

[CH3:1][C:2]1([CH3:23])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:9]=2)[NH:4][CH:3]1[C:16]1[CH:17]=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=1.[CH3:24][O:25][C:26](=[O:31])[C:27](Br)([CH3:29])[CH3:28].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:24][O:25][C:26](=[O:31])[C:27]([NH:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([CH:3]2[C:2]([CH3:23])([CH3:1])[CH2:11][C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:12]([F:15])([F:13])[F:14])[CH:9]=3)[NH:4]2)[CH:17]=1)([CH3:29])[CH3:28]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 3-(3,3-dimethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine (1.5 g, 4.7 mmol), 2-bromo-2-methyl-propionic acid methyl ester (2.55 g, 14.1 mmol) and potassium carbonate (3.24 g, 23.5 mmol) in N,N-dimethylformamide (12 mL) was stirred at 25° C. for 5 d. Then the reaction mixture was extracted with ethyl acetate (2×100 mL), washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification on flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company)(30% ethyl acetate/hexanes) to afford 2-[3-(3,3-dimethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamino]-2-methyl-propionic acid methyl ester (400 mg, 20%) as a brown oil. LC/MS m/e calcd for C23H27F3N2O2 (M+H)+: 421.48, observed: 421.1.

Workup

extractionThen the reaction mixture was extracted with ethyl acetate (2×100 mL)
washwashed with water
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customPurification on flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company)(30% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-7e7333c436f4431fa575c789c86d1b65
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586747B2

Reaction notes

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