Potassium Phosphate, Tribasic → HCID 117601911, compound

HRID 1773699Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]2[CH2:10][CH2:9]2)[C:3]=1[C:11]1[C:19]2[NH:18][C:17](=[O:20])[NH:16][C:15]=2[CH:14]=[C:13]([C:21]2[C:22]([CH3:27])=[N:23][O:24][C:25]=2[CH3:26])[CH:12]=1.[CH:28]1(B(O)O)[CH2:30][CH2:29]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.ClCCl.[Pd+2].ClC1C=C[C-](P(C2C=CC=CC=2)C2C=CC=CC=2)C=1Cl.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH:8]1([C:4]2[C:3]([C:11]3[C:19]4[NH:18][C:17](=[O:20])[NH:16][C:15]=4[CH:14]=[C:13]([C:21]4[C:22]([CH3:27])=[N:23][O:24][C:25]=4[CH3:26])[CH:12]=3)=[C:2]([CH:28]3[CH2:30][CH2:29]3)[CH:7]=[CH:6][N:5]=2)[CH2:10][CH2:9]1

Participants

Conditions

Temperature: 100 °C

Procedure

4-(4-bromo-2-cyclopropylpyridin-3-yl)-6-(3,5-dimethylisoxazol-4-yl)-1H-benzo[d]imidazol-2(3H)-one (17 mg, 0.04 mmol) and cyclopropyl boronic acid (100 mg, 1.2 mmol) were dissolved in dioxane (2 mL). To the reaction mixture were added K3PO4 (50 mg, 0.24 mol) and dichloro 1,1′-bis(diphenylphosphino)ferrocene palladium (II) dichloromethane (10 mg, 0.012 mmol). The reaction mixture was heated at 100° C. for 3 h. Solvent was evaporated, the residue was dissolved in EtOAc, washed with brine, evaporated organic solvent and the residue was purified with Prep HPLC (0-100% CH3CN/H2O) to afford 5.4 mg of 4-(2,4-dicyclopropylpyridin-3-yl)-6-(3,5-dimethylisoxazol-4-yl)-1H-benzo[d]imidazol-2(3H)-one.

Workup

customSolvent was evaporated
dissolutionthe residue was dissolved in EtOAc
washwashed with brine
customevaporated organic solvent
customthe residue was purified with Prep HPLC (0-100% CH3CN/H2O)

Sources & evidence

ORD record: ord-ac4fa3937be64a0d9118e698243fa9d7
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255089B2

Reaction notes

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