Potassium Carbonate → HCID 178518544, compound

HRID 474807Notes

Reaction equation

HRID 474807 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15]Cl)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18].[N:21]1([CH2:30][C:31]2[C:32](=[O:38])[NH:33][C:34](=[S:37])[NH:35][CH:36]=2)[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][S:37][C:34]3[NH:35][CH:36]=[C:31]([CH2:30][N:21]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[CH:23]=[CH:22]4)[C:32](=[O:38])[N:33]=3)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 668255374-(Chloromethyl)phenyl 4-chloro-3-(trifluoromethyl)phenyl etherHCID 86666220HCID 86666220, compound

Product 1

HCID 178518544HCID 178518544, compoundYield 8.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-chloro-4-(4-(chloromethyl)phenoxy)-2-(trifluoromethyl)benzene (200 mg, 0.623 mmol), 5-(1H-indol-1-ylmethyl)-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone (160 mg, 0.623 mmol), and K2CO3 (200 mg, 1.447 mmol) in DMF (5 mL) was heated at 80° C. for 3 h. Purification via MDAP then afforded the title compound (30 mg, 8.44% yield). LCMS: rt=4.19 min, [M+H+]=542

Workup

  1. customPurification via MDAP

Sources & evidence

ORD record
ord-01e69f81d4734a508d3f057671d806e1
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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