Potassium Carbonate → HCID 58913125, compound

HRID 1296681Notes

Reaction equation

HRID 1296681 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[O:8][C:7](=[O:14])[C:6]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1)=[C:5]2[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:28][CH:27]=1.[C:39]([O-])([O-])=O.[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:13][O:12][C:11]1[CH:10]=[C:9]2[C:4]([C:5]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:28][CH:27]=3)=[C:6]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[C:7](=[O:14])[O:8]2)=[CH:3][C:2]=1[CH3:39]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 58913074HCID 58913074, compound

Product 1

HCID 58913125HCID 58913125, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2,2-dimethyl-propionic acid 4-(6-bromo-7-methoxy-2-oxo-3-(4-trifluoromethyl-phenyl)-2H-chromen-4-ylmethyl)-phenyl ester (100 mg, 0.17 mmol), K2CO3 (70 mg, 0.51 mmol), trimethylboroxine (24 μL, 0.17 mmol) and Pd(Ph3P)4 (20 mg, 0.017 mmol) in anhydrous dioxane (2 mL) was stirred at reflux temperature for 2 h. After cooling to room temperature, the resultant suspension was filtered over Celite, and the solvent was removed in vacuo. The residue was recrystallized from CH2Cl2/hexane to afford the desired compound as a beige solid (72 mg, 82%) displaying. 1H NMR (300 MHz, CDCl3) δ 7.62 (d, J=8.0 Hz, 2H), 7.36 (d, J=8.0 Hz, 2H), 7.22 (d, J=0.9 Hz, 1H), 7.04 (d, J=8.8 Hz, 2H), 6.96 (d, J=8.8 Hz, 2H), 6.83 (s, 1H), 4.02 (s, 2H), 3.91 (s, 3H), 2.16 (s, 3H), 1.35 (s, 9H); MS (ESI) m/z 524.9 (M+H)+, HPLC tR 7.81 min.

Workup

  1. temperatureat reflux temperature for 2 h
  2. filtrationthe resultant suspension was filtered over Celite
  3. customthe solvent was removed in vacuo
  4. customThe residue was recrystallized from CH2Cl2/hexane

Sources & evidence

ORD record
ord-4dd988b6d0ba490f9c13196e80633290
Source dataset
uspto-grants-2007_07
Patent number
US07247646B2

Reaction notes

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