3-(Trifluoromethyl)phenol → 4-(2-Nitro-5-(piperidin-1-yl)phenyl)-6-(3-(trifluoromethyl)phenoxy)pyrimidine

HRID 625228Notes

Reaction equation

[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:19]1[CH:24]=[C:23]([C:25]2[CH:30]=[C:29]([N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)[CH:28]=[CH:27][C:26]=2[N+:37]([O-:39])=[O:38])[N:22]=[CH:21][N:20]=1>CN(C=O)C>[N+:37]([C:26]1[CH:27]=[CH:28][C:29]([N:31]2[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]2)=[CH:30][C:25]=1[C:23]1[CH:24]=[C:19]([O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=2)[N:20]=[CH:21][N:22]=1)([O-:39])=[O:38]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 160 mg of 3-(trifluoromethyl)phenol in 2 mL of DMF was added 104 mg of potassium carbonate and 160 mg of intermediate 3.1b. After stirring overnight at 50° C. the reaction mixture was partitioned between water and ethyl acetate. The organic extracts were washed with brine and dried (Na2SO4). The solvent was evaporated to give a yellow syrup that was used directly in the next step.

Workup

customwas partitioned between water and ethyl acetate
washThe organic extracts were washed with brine
dry with materialdried (Na2SO4)
customThe solvent was evaporated
customto give a yellow syrup that

Sources & evidence

ORD record: ord-c1bb09c366d94cae8f09f85393383e0f
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09301951B2

Reaction notes

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