Potassium Carbonate → HCID 57824463, compound

HRID 708947Notes

Reaction equation

Br[C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=2)[CH:6]=1.[C:18]([C:21]1[CH:22]=[CH:23][C:24]([F:30])=[C:25](B(O)O)[CH:26]=1)(=[O:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCOCC1>[F:30][C:24]1[CH:25]=[CH:26][C:21]([C:18](=[O:20])[CH3:19])=[CH:22][C:23]=1[C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=2)[CH:6]=1

Participants

Conditions

Temperature: 150 °C

Procedure

4-Bromo-1-(4-trifluoromethoxyphenyl)-1H-imidazole (200 mg, 0.651 mmol), 5-acetyl-2-fluorophenylboronic acid (178 mg, 0.977 mmol), tetrakis(triphenylphosphine)-palladium(0) (7 mg, 0.007 mmol), a 2 N aqueous solution of potassium carbonate (0.651 mL) and dioxane (8 mL) were combined and added to a microwave vessel. The reaction mixture was heated in the microwave with stirring to 150° C. for 20 min. LC-MS indicated 88% anticipated product; TLC (1:1 hexanes:EtOAc) indicated the presence of starting material plus 3 other materials. EtOAc and H2O were added to the reaction mixture. The aqueous layer was extracted with EtOAc, and the organic extracts were washed with brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by chromatography with gradient elution (100% hexanes to 100% EtOAc) resulting in an off-white solid (90 mg): mp 129° C.; ESIMS m/z 265.0 (M+H).

Workup

additionadded to a microwave vessel
temperatureThe reaction mixture was heated in the microwave

Sources & evidence

ORD record: ord-6c01a17599d1448796bec5a49bae9451
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09179681B2

Reaction notes

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