Dichloromethane → 6-(3,5-dimethylisoxazol-4-yl)-4-(1-ethyl-4-methyl-1H-pyrazol-5-yl)-1H-benzo[d]imidazol-2(3H)-one

HRID 1773717Notes

Reaction equation

[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9](B3OC(C)(C)C(C)(C)O3)[C:10]3[NH:14][C:13](=[O:15])[NH:12][C:11]=3[CH:16]=2)=[C:5]([CH3:26])[O:4][N:3]=1.Br[C:28]1[N:32]([CH2:33][CH3:34])[N:31]=[CH:30][C:29]=1[CH3:35].C(Cl)Cl.C1CCN2C(=NCCC2)CC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CS(C)=O.O>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:28]3[N:32]([CH2:33][CH3:34])[N:31]=[CH:30][C:29]=3[CH3:35])[C:10]3[NH:14][C:13](=[O:15])[NH:12][C:11]=3[CH:16]=2)=[C:5]([CH3:26])[O:4][N:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a microwave vial containing 6-(3,5-dimethylisoxazol-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-one (40 mg, 0.11 mmol, 1 equiv.) were added 5-bromo-1-ethyl-4-methyl-1H-pyrazole 11 (64 mg, 0.34 mmol, 3 equiv.), Pd(dppf)Cl2. CH2Cl2 (9 mg, 0.011 mmol, 0.1 equiv.), DBU (101 μL, 6 equiv.) and DMSO-H2O (4 mL, 0.2 M, 2/1, v/v). The mixture was heated to 120° C. for 30 min in microwave. The reaction was concentrated under reduced pressure and purification was carried out by reverse phase HPLC.

Workup

concentrationThe reaction was concentrated under reduced pressure and purification

Sources & evidence

ORD record: ord-f3bb7a628eb5428591b6b845e0b1bf31
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255089B2

Reaction notes

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