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

HRID 2401229
Notes
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Reaction equation

HRID 2401229 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 709434,6-DichloropyrimidineHCID 58126817(2-(Trifluoromethyl)-1h-indol-5-yl)methanamine2×

Product 1

HCID 51356699N-(6-Chloro-4-pyrimidinyl)-2-(trifluoromethyl)-1H-indole-5-methanamineYield 74.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. extractionextracted with ethyl acetate
  2. customTraces of water were removed with a phase separator
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes