Dimethyl Sulfoxide → N-(6-Chloro-4-pyrimidinyl)-2-(trifluoromethyl)-1H-indole-5-methanamine

HRID 2401229Notes

Reaction equation

[F:1][C:2]([F:15])([F:14])[C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][NH2:13])=[CH:7][CH:6]=2.[Cl:16][C:17]1[CH:22]=[C:21](Cl)[N:20]=[CH:19][N:18]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[Cl:16][C:17]1[N:18]=[CH:19][N:20]=[C:21]([NH:13][CH2:12][C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[NH:4][C:3]([C:2]([F:1])([F:14])[F:15])=[CH:11]3)[CH:22]=1

Participants

Conditions

Temperature: 140 °C

Procedure

{[2-(Trifluoromethyl)-1H-indol-5-yl]methyl}amine (Intermediate 34, 600 mg, 2.394 mmol), 4,6-dichloropyrimidine (357 mg, 2.394 mmol) and potassium carbonate (993 mg, 7.18 mmol) were added to DMSO (13 mL). The reaction mixture was heated in the microwave for 1.5 hours at 140° C. The LC/MS showed product. The reaction mixture was poured into water and extracted with ethyl acetate. Traces of water were removed with a phase separator and the solvent removed under reduced pressure to give the title compound (580 mg);

Workup

extractionextracted with ethyl acetate
customTraces of water were removed with a phase separator
customthe solvent removed under reduced pressure

Sources & evidence

ORD record: ord-1d5291ed946a4fca83592fbda4862b5d
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796283B2

Reaction notes

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