Potassium Carbonate → HCID 44472980, compound

HRID 2104801Notes

Reaction equation

[CH2:1]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[C:18]1[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1)=[CH:15][CH:14]=[CH:13][C:12]=2[C:25]([F:28])([F:27])[F:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:30]1[CH:31]=[C:32]([CH:37]=[CH:38][CH:39]=1)[C:33]([O:35][CH3:36])=[O:34].C([O-])([O-])=O.[K+].[K+]>N1C=CC=CC=1.O>[CH2:1]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[C:18]1[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=1)[O:24][C:30]1[CH:31]=[C:32]([CH:37]=[CH:38][CH:39]=1)[C:33]([O:35][CH3:36])=[O:34])=[CH:15][CH:14]=[CH:13][C:12]=2[C:25]([F:28])([F:26])[F:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 3-[3-benzyl-8-(trifluoromethyl)quinolin-4-yl]phenol (2.65 g, 7.0 mmol), methyl 3-bromobenzoate (3.01 g, 14.0 mmol), CuO (1.01 g, 12.6 mol), and K2CO3 (1.93 g, 14.0 mmol) in dry pyridine (17.5 mL) are heated under nitrogen at 120° C. for 48 h. The cooled reaction is diluted with water (100 mL) and extracted with ether (2×100 mL). The dried (MgSO4) extracts are concentrated to a dark oil which is chromatographed on silica gel using 20:80 ethyl acetate:hexane as eluent isolating the title compound as a colorless tacky solid (Rf˜0.3, 1.53 g). MS (ESI) m/z 514; HRMS: calcd for C31H22F3NO3+H+, 514.16245; found (ESI, [M+H]+), 514.1638.

Workup

customThe cooled reaction
extractionextracted with ether (2×100 mL)
dry with materialThe dried (MgSO4) extracts
concentrationare concentrated to a dark oil which
customis chromatographed on silica gel using 20:80 ethyl acetate

Sources & evidence

ORD record: ord-0054709ea2734c3a83aedcb652ce5cca
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576215B2

Reaction notes

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