Diisopropylamine → HCID 66690205, compound

HRID 592315Notes

Reaction equation

[NH2:1][C:2]1[C:11]([OH:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1Br.[F:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.[Na+].[Na+].[Na+].P(C1C=C(S([O-])(=O)=O)C=CC=1)(C1C=C(S([O-])(=O)=O)C=CC=1)C1C=C(S([O-])(=O)=O)C=CC=1.C(NC(C)C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O.CN(C)C=O>[NH2:1][C:2]1[C:3]([C:18]2[CH:19]=[CH:20][C:15]([F:14])=[CH:16][CH:17]=2)=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][C:11]=1[OH:12]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of methyl 4-amino-3-bromo-5-hydroxybenzoate (1.0 g, 4.06 mmol), (4-fluorophenyl)-boronic acid (0.85 g, 6.1 mmol), 3,3′,3″-phosphinidynetris (benzensulfonic acid) trisodium salt (195.0 mg, 0.31 mmol), palladium(II) acetate (23.0 mg, 0.10 mmol) and diisopropylamine (0.58 mL, 4.06 mmol) were added N,N-dimethylformamide (15.2 mL) and water (5.1 mL). The mixture was heated to 80° C. After 18 h, the mixture was cooled to ambient temperature and ethyl acetate was added. The organic layer was washed with water (3×), brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→50% hexanes/ethyl acetate) gave the title compound (0.27 g). LC-MS [M+1]=262.2.

Workup

temperaturethe mixture was cooled to ambient temperature
washThe organic layer was washed with water (3×), brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customPurification by silica gel chromatography (100% hexanes→50% hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-7e527773a32543e8bc445e618f1b3284
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238647B2

Reaction notes

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