Sodium Carbonate → HCID 18628527, compound

HRID 1060528Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[C:5]([CH3:19])=[CH:4][N:3]=1.[F:20][C:21]([F:32])([F:31])[C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C(=O)([O-])[O-:34].[Na+].[Na+]>C(COC)OC.ClCCl.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:19][C:5]1[C:6]([C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)=[O:34])=[N:7][C:2]([C:25]2[CH:26]=[CH:27][C:22]([C:21]([F:31])([F:32])[F:20])=[CH:23][CH:24]=2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The title compound of Example 1, Step A (0.6 g, 2 mmol), 4-trifluoromethyl-benzeneboronic acid (1.1 g, 6 mmol), and bis(triphenylphosphine)palladium dichloride were dissolved in dimethoxyethane (15 mL) and aqueous sodium carbonate (2 M, 4 mmol). The resulting mixture was heated at 80° C. for 3 h. The mixture was diluted with dichloromethane (50 mL) and water (50 mL). The dichloromethane layer was dried over magnesium sulfate, concentrated under reduced pressure, and the residue was subjected to silica gel chromatography using hexaneslethyl acetate (85:15). The title compound of Step A, a compound of the invention, was isolated as a white solid (0.56 g) melting at 159-161° C. 1H NMR (CDCl3/200 MHz) 2.47 (s, 3H), 7.62-7.78 (m, 3H), 7.94 (d, 1H), 8.17 (d, 1H), 8.34 (s, 1H), 8.5 (d, 2H), 8.9 (s, 1H).

Workup

dry with materialThe dichloromethane layer was dried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-de8bd4910d1a4b128fbe3759a0e7deae
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525001B1

Reaction notes

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