Potassium Carbonate → HCID 59596694, compound

HRID 2264791Notes

Reaction equation

HRID 2264791 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Br[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>>[F:27][C:23]1[CH:22]=[C:21]([CH2:20][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[N:13]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]=[CH:10][CH:9]=3)=[CH:6][CH:7]=2)[CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 680073-Fluorobenzyl bromideHCID 135985748HCID 135985748, compound

Product 1

HCID 59596694HCID 59596694, compoundYield 76.4%

Procedure

A solution of ethyl 6-(4-hydroxyphenyl)-2-pyridinecarboxylate (D2, 100 mg, 0.41 mmol), 1-(bromomethyl)-3-fluorobenzene (117 mg, 0.62 mmol) and potassium carbonate (138 mg, 1.0 mmol) was stirred at 60° C. for 4 h. Then the solvent was evaporated under reduced pressure and the resulting crude material was purified by chromatography on silica gel using ethyl acetate/cyclohexanes (1:1) to afford the title compound (110 mg, 76%); MS: (ES/+) m/z: 352 [MH+], C21H18FNO3 requires 351; 1H-NMR (300 MHz, CDCl3) δ (ppm): 8.05 (d, 2H), 8.0 (m, 1H), 7.80 (d, 2H), 7.35 (m, 1H), 7.20 (m, 2H), 7.05 (d, 2H), 7.00 (m, 1H), 5.15 (s, 2H), 4.50 (q, 2H), 1.45 (t, 3H).

Workup

  1. customThen the solvent was evaporated under reduced pressure
  2. customthe resulting crude material was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-7adde7e8b5504f5096e93437a8fa29f0
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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