Dichloromethane → 4-(8-chloro-6-methylquinolin-5-yl)-6-(3,5-dimethylisoxazol-4-yl)-1H-benzo[d]imidazol-2(3H)-one

HRID 1773678Notes

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[C:37]([CH3:38])=[CH:36][C:35]([Cl:39])=[C:34]2[C:29]=1[CH:30]=[CH:31][CH:32]=[N:33]2.C(Cl)Cl.N1(C2CCCCCCCCCC2)CCCN=CCCCCC1>CS(C)=O.O.C1COCC1>[Cl:39][C:35]1[CH:36]=[C:37]([CH3:38])[C:28]([C:9]2[C:10]3[NH:14][C:13](=[O:15])[NH:12][C:11]=3[CH:16]=[C:7]([C:6]3[C:2]([CH3:1])=[N:3][O:4][C:5]=3[CH3:26])[CH:8]=2)=[C:29]2[C:34]=1[N:33]=[CH:32][CH:31]=[CH:30]2

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 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 (100.0, 0.282 mmol) and 5-bromo-8-chloro-6-methylquinoline (72.2 mg, 0.282 mmol) was treated with PdCl2dppf.CH2Cl2 (20.9 mg, 0.028 mmol) in the presence of 1,8-Diazabicycloundec-7-ene (DBU, 204.0 mg, 1.34 mmol, 4.76 equiv) in DMSO (0.2 mL) and water (0.2 mL). The reaction mixture was heated at 120° C. in oil bath. The reaction mixture was diluted with THF (3 mL) and purified by Gilson preparative HPLC to give 4-(8-chloro-6-methylquinolin-5-yl)-6-(3,5-dimethylisoxazol-4-yl)-1H-benzo[d]imidazol-2(3H)-one

Workup

custompurified by Gilson preparative HPLC

Sources & evidence

ORD record: ord-d31ff286e72544409a28b58cde7e2ea9
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255089B2

Reaction notes

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