Potassium Carbonate → HCID 67488107, compound

HRID 1880566Notes

Reaction equation

[NH2:1][C:2]1[CH:11]=[CH:10][C:9](Br)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C([O-])([O-])=O.[K+].[K+].[F:19][C:20]([F:32])([F:31])[O:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1>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.COCCOC.O>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([C:25]2[CH:24]=[CH:23][C:22]([O:21][C:20]([F:19])([F:31])[F:32])=[CH:27][CH:26]=2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

Conditions

Temperature: 90 °C

Procedure

A DME/water solution (40 mL, 3/1) containing methyl 2-amino-5-bromobenzoate (2.5 g, 12.3 mmol), K2CO3 (4.0 g, 24.6 mmol), 4-(trifluoromethoxy)phenyl boronic acid (3.8 g, 18.5 mmol) and Pd(PPh3)4 (0.712 g, 0.62 mmol) was heated at 90° C. under an argon atmosphere. After approximately 1 hour the solution was cooled to room temperature and partitioned between water and ethyl acetate. The organic phase was washed with water, brine and dried over Na2SO4. The solution was filtered, concentrated and the residue purified by silica gel chromatography using a hexanes/ethyl acetate gradient to give the title compound. 1H NMR (500 MHz, CDCl3): δ 8.12 (d, J=2.2 Hz, 1H); 7.57 (d, J=8.5 Hz, 2H); 7.52 (dd, J=2.2, 8.5 Hz, 1H); 7.28 (d, J=8.5 Hz, 2H); 6.77 (d, J=8.5 Hz, 1H); 5.84 (broad s, 2H); 3.94 (s, 3H). LCMS1 3.91 min. (M+H)=312

Workup

temperatureAfter approximately 1 hour the solution was cooled to room temperature
custompartitioned between water and ethyl acetate
washThe organic phase was washed with water, brine
dry with materialdried over Na2SO4
filtrationThe solution was filtered
concentrationconcentrated
customthe residue purified by silica gel chromatography

Sources & evidence

ORD record: ord-6e2c4cf088bf41af97a093fdac19f05c
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318760B2

Reaction notes

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