Phenol → HCID 44192600, compound

HRID 1855343Notes

Reaction equation

HRID 1855343 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].Cl[C:13]1[CH:18]=[C:17]([CH3:19])[N:16]=[C:15]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH:31]=[C:30]([CH3:32])[N:29]=[CH:28]3)=[C:23]([O:33][CH3:34])[CH:22]=2)[N:14]=1.C1(O)C=CC=CC=1.[H-].[Na+]>>[CH3:34][O:33][C:23]1[CH:22]=[C:21]([NH:20][C:15]2[N:16]=[C:17]([CH3:19])[CH:18]=[C:13]([O:9][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:2]([F:10])([F:11])[F:1])[N:14]=2)[CH:26]=[CH:25][C:24]=1[N:27]1[CH:31]=[C:30]([CH3:32])[N:29]=[CH:28]1

Participants

5

Reactant 4

HCID 996PhenolHCID 24758Sodium hydrideHCID 679582-TrifluoromethylphenolHCID 57829826HCID 57829826, compound

Product 1

HCID 44192600HCID 44192600, compound

Procedure

The title compound was prepared in analogous manners as described in example 9 from 2-trifluoromethyl-phenol and (4-chloro-6-methyl-pyrimidin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine. The reaction was heated for 3.5 h to 200° C. in a microwave oven. Several times the phenol (overall 4.4 equivalents) and additional sodium hydride had to be added in order to obtain complete conversion. The title compound was obtained, after purification by column chromatography on silica gel using dichloromethane/methanol (19:1 v/v) as eluent, as a white solid in 15% yield.

Workup

  1. customThe title compound was prepared in analogous manners
  2. temperatureThe reaction was heated for 3.5 h to 200° C. in a microwave oven
  3. additionto be added in order
  4. customto obtain complete conversion

Sources & evidence

ORD record
ord-9ea4402b7f6145769d4ddb018be900db
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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