Water → HCID 57510040, compound

HRID 624175Notes

Reaction equation

[CH:1]([B-](F)(F)F)=[CH2:2].[K+].Br[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH2:14][N:13]([C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:32])[NH:28][CH2:29][CH2:30][CH3:31])=[CH:23][CH:22]=1)=[O:19])[CH2:12]2.C(=O)(O)[O-].[Na+].O>CN(C)C=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>[CH2:29]([NH:28][C:27]([C:24]1[CH:23]=[CH:22][C:21]([NH:20][C:18]([N:13]2[CH2:12][C:11]3[C:15](=[CH:16][CH:17]=[C:9]([CH:1]=[CH2:2])[CH:10]=3)[CH2:14]2)=[O:19])=[CH:26][CH:25]=1)=[O:32])[CH2:30][CH3:31]

Participants

Conditions

Temperature: 85 °C

Procedure

In a sealed vial under nitrogen, a mixture of potassium vinyltrifluoroborate (100 mg, 0.75 mmol), 5-bromo-N-(4-(propylcarbamoyl)phenyl)isoindoline-2-carboxamide (150 mg, 0.37 mmol), bis(triphenylphosphine)palladium(II) chloride and saturated aqueous sodium bicarbonate (0.62 ml) in dimethylformamide was heated at 85° C. for 5 hours. The reaction was poured into water, filtered, dried and purified by reverse-phase chromatography to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.57 (s, 1H), 8.25 (t, J=5.7 Hz, 1H), 7.75-7.78 (m, 2H), 7.63-7.67 (m, 2H), 7.47 (s, 1H), 7.42 (dd, J=7.9, 1.5 Hz, 1H), 7.34 (d, J=7.8 Hz, 1H), 6.77 (dd, J=17.6, 10.9 Hz, 1H), 5.85 (dd, J=17.6, 1.0 Hz, 1H), 5.27 (d, J=11.0 Hz, 1H), 4.77-4.78 (bs, 4H), 3.16-3.22 (m, 2H), 1.46-1.59 (m, 2H), 0.89 (t, J=7.4 Hz, 3H); MS (ESI(+)) m/e 350 (M+H)+.

Workup

filtrationfiltered
customdried
custompurified by reverse-phase chromatography

Sources & evidence

ORD record: ord-e463599a1ced4b3bb18f5a1b8c3ffa84
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09302989B2

Reaction notes

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