Cesium carbonate → HCID 117601762, compound

HRID 1773745Notes

Reaction equation

HRID 1773745 reaction equation
Cl[C:2]1[C:7]2[N:8]([CH3:12])[C:9](=[O:11])[NH:10][C:6]=2[CH:5]=[C:4]([C:13]2[C:14]([CH3:19])=[N:15][O:16][C:17]=2[CH3:18])[CH:3]=1.CC1(C)C(C)(C)OB([C:28]2[C:37]([C:38]([F:41])([F:40])[F:39])=[CH:36][CH:35]=[C:34]3[C:29]=2[CH:30]=[CH:31][C:32](=O)[NH:33]3)O1.C([O-])([O-])=[O:45].[Cs+].[Cs+]>ICCC.COCCOC.O>[CH3:19][C:14]1[C:13]([C:4]2[CH:3]=[C:2]([C:36]3[CH:35]=[C:34]4[C:29]([CH:30]=[CH:31][CH:32]=[N+:33]4[O-:45])=[CH:28][C:37]=3[C:38]([F:41])([F:40])[F:39])[C:7]3[N:8]([CH3:12])[C:9](=[O:11])[NH:10][C:6]=3[CH:5]=2)=[C:17]([CH3:18])[O:16][N:15]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 117601747HCID 117601747, compoundHCID 131734712HCID 131734712, compound

Product 1

HCID 117601762HCID 117601762, compound

Reagents, catalysts & solvents 2

HCID 336431-IodopropaneCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a microwave vial containing 7-chloro-5-(3,5-dimethylisoxazol-4-yl)-1-methyl-1H-benzo[d]imidazol-2(3H)-one (100 mg, 0.36 mmol, 1 equiv.) was added 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)quinolone (350 mg, 1.08 mmol, 3 equiv.), Cs2CO3 (704 mg, 2.16 mmol, 6 equiv.) and PEPPSI™-IPr catalyst (98 mg, 0.14 mmol, 0.4 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 carried out by reverse phase HPLC.

Workup

  1. concentrationThe reaction was concentrated in vacuo and purification

Sources & evidence

ORD record
ord-31c66fd1d4bb4e689f3f22a80045adb8
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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