Potassium Carbonate → HCID 178480219, compound

HRID 474808Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][C:12]2[C:13](=[O:19])[NH:14][C:15](=[S:18])[NH:16][CH:17]=2)=[CH:3]1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([CH2:34]Cl)=[CH:30][CH:29]=2)=[CH:23][C:22]=1[C:36]([F:39])([F:38])[F:37].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CC(=O)OCC>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:29]=[CH:30][C:31]([CH2:34][S:18][C:15]3[NH:16][CH:17]=[C:12]([CH2:11][C:4]4[C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[N:2]([CH3:1])[CH:3]=4)[C:13](=[O:19])[N:14]=3)=[CH:32][CH:33]=2)=[CH:23][C:22]=1[C:36]([F:37])([F:38])[F:39]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-[(1-methyl-1H-indol-3-yl)methyl]-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone (95 mg, 0.349 mmol), 1-chloro-4-(4-(chloromethyl)phenoxy)-2-(trifluoromethyl)benzene (112 mg, 0.349 mmol), and K2CO3 (90 mg, 0.651 mmol) in DMF (2 mL) was heated at 80° C. for 3 h. The reaction mixture was diluted with EA (10 mL) and filtered through a silica pad to remove the solid suspension. The clear filtrate was concentrated under reduced pressure and purification via MDAP then afforded the title compound (50 mg, 24.75% yield). LCMS: rt=4.79 min, [M+H+]=556

Workup

filtrationfiltered through a silica pad
customto remove the solid suspension
concentrationThe clear filtrate was concentrated under reduced pressure and purification via MDAP

Sources & evidence

ORD record: ord-f8b42511865544ccbefeff4737562f10
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637536B2

Reaction notes

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