Cesium carbonate → 5-(3,5-dimethylisoxazol-4-yl)-1-methyl-7-(6-(trifluoromethyl)quinolin-5-yl)-1H-benzo[d]imidazol-2(3H)-one

HRID 1773723Notes

Reaction equation

[CH3:1][C:2]1[C:6]([C:7]2[CH:17]=[C:16](B3OC(C)(C)C(C)(C)O3)[C:10]3[N:11]([CH3:15])[C:12](=[O:14])[NH:13][C:9]=3[CH:8]=2)=[C:5]([CH3:27])[O:4][N:3]=1.Br[C:29]1[C:38]([C:39]([F:42])([F:41])[F:40])=[CH:37][CH:36]=[C:35]2[C:30]=1[CH:31]=[CH:32][CH:33]=[N:34]2.C([O-])([O-])=O.[Cs+].[Cs+]>ICCC.COCCOC.O>[CH3:1][C:2]1[C:6]([C:7]2[CH:17]=[C:16]([C:29]3[C:38]([C:39]([F:40])([F:41])[F:42])=[CH:37][CH:36]=[C:35]4[C:30]=3[CH:31]=[CH:32][CH:33]=[N:34]4)[C:10]3[N:11]([CH3:15])[C:12](=[O:14])[NH:13][C:9]=3[CH:8]=2)=[C:5]([CH3:27])[O:4][N:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a microwave vial containing 5-(3,5-dimethylisoxazol-4-yl)-1-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-one (30 mg, 0.08 mmol, 1 equiv.) was added 5-bromo-6-(trifluoromethyl)quinoline (68 mg, 0.24 mmol, 3 equiv.), Cs2CO3 (105 mg, 0.33 mmol, 4 equiv.) and PEPPSI™-IPr catalyst (11 mg, 0.016 mmol, 0.2 equiv.) and dissolved in DME-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 in vacuo and purification was then carried out by reverse phase HPLC.

Workup

concentrationThe reaction was concentrated in vacuo and purification

Sources & evidence

ORD record: ord-05a6d3500511487391e290db3d3909c3
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255089B2

Reaction notes

Loading…