Phenylboronic Acid → HCID 136414055, compound

HRID 2036778Notes

Reaction equation

[F-].[K+].[C:3]1(B(O)O)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[C:15](=[O:27])[NH:16][C:17]([C:23]([F:26])([F:25])[F:24])=[N:18]2>C1COCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>[C:3]1([C:13]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:14]=2[C:15](=[O:27])[NH:16][C:17]([C:23]([F:24])([F:25])[F:26])=[N:18]3)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Palladium (II) acetate (19 mg, 0.085 mmol), potassium fluoride (498 mg, 8.57 mmol), 2-(di-tert-butylphosphino)biphenyl (51.1 mg, 0.171 mmol), and phenylboronic acid (522 mg, 4.27 mmol) were combined in a microwave vial under an argon atmosphere. A solution of 5-chloro-2-(trifluoromethyl)quinazolin-4(3H)-one (710 mg, 2.86 mmol) in dry THF (9 mL) was added and the mixture was heated in the microwave at 100° C. for 30 min. After this time, the reaction mixture was diluted with ethyl acetate (50 mL) and washed with 1N NaOH (25 mL) and saturated NaCl (25 mL). The organic layer was separated, dried over sodium sulfate and then concentrated under reduced pressure to give the crude product (968 mg), which was used in the next step without further purification.

Workup

washwashed with 1N NaOH (25 mL) and saturated NaCl (25 mL)
customThe organic layer was separated
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-278c8c3f0b9e4080bb26ba9e5da4f1e1
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575184B2

Reaction notes

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