Potassium Carbonate → HCID 67443553, compound

HRID 2045221Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 2-(3-amino-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonitrile (0.64 g, 2.3 mmol), 2-bromo-2-methyl-propionic acid methyl ester (1.25 g, 6.9 mmol) and potassium carbonate (1.59 g, 11.5 mmol) in N,N-dimethylformamide (6 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-(6-cyano-3,3-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamino]-2-methyl-propionic acid methyl ester (500 mg, 43%) as a brown oil: LC/MS m/e calcd for C23H27N3O2 (M+H)+: 378.49, observed: 378.2.

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-2f07bb4a415a40f9b2f42725d597a3e9
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586747B2

Reaction notes

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