Hydrochloric Acid → HCID 67017324, compound

HRID 1842043Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:20]3[C:15](=[CH:16][C:17]([C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=4)=[CH:18][CH:19]=3)[CH2:14][C:13]([CH3:32])([CH3:31])[CH2:12]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[F:33].[Cu][C:35]#[N:36].Cl>CN(C)C=O>[CH3:32][C:13]1([CH3:31])[CH2:14][C:15]2[C:20](=[CH:19][CH:18]=[C:17]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:28])([F:30])[F:29])=[CH:23][CH:22]=3)[CH:16]=2)[N:11]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([C:35]#[N:36])=[C:3]([F:33])[CH:4]=2)(=[O:10])=[O:9])[CH2:12]1

Participants

Conditions

Temperature: 200 °C

Procedure

710 mg 1-(4-Bromo-3-fluoro-benzenesulfonyl)-3,3-dimethyl-6-(4-trifluoromethyl-phenyl)-1,2,3,4-tetrahydro-quinoline and 123 mg copper(I)cyanide were dissolved in 1.5 ml dimethylformamide and heated to 200° C. under microwave irradiation for thirty minutes. The cooled reaction mixture was poured into 50 ml 2M hydrochloric acid and extracted five times with portions of 20 ml ethyl acetate. The combined organic layers were dried over MgSO4. The solvent was evaporated in vacuo and the residue purified by chromatography on silica gel to obtain 481 mg 4-[3,3-Dimethyl-6-(4-trifluoromethyl-phenyl)-3,4-dihydro-2H-quinoline-1-sulfonyl]-2-fluoro-benzonitrile.

Workup

customThe cooled reaction mixture
extractionextracted five times with portions of 20 ml ethyl acetate
dry with materialThe combined organic layers were dried over MgSO4
customThe solvent was evaporated in vacuo
customthe residue purified by chromatography on silica gel

Sources & evidence

ORD record: ord-711852350cca4779868193637d2f1c16
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946212B2

Reaction notes

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