Cesium carbonate → 4-(2-(4-(Benzo[D]thiazol-2-ylamino)phenoxy)pyridin-3-YL)cyclohexanol

HRID 410238Notes

Reaction equation

HRID 410238 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+].F[C:25]1[C:30]([CH:31]2[CH2:36][CH2:35][CH:34]([OH:37])[CH2:33][CH2:32]2)=[CH:29][CH:28]=[CH:27][N:26]=1>CN1C(=O)CCC1.O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:25]2[C:30]([CH:31]3[CH2:32][CH2:33][CH:34]([OH:37])[CH2:35][CH2:36]3)=[CH:29][CH:28]=[CH:27][N:26]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 585477094-(2-Fluoropyridin-3-yl)cyclohexanolHCID 593268134-(Benzo[d]thiazol-2-ylamino)phenol

Product 1

HCID 593269514-(2-(4-(Benzo[D]thiazol-2-ylamino)phenoxy)pyridin-3-YL)cyclohexanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

To a vial containing 4-(benzo[d]thiazol-2-ylamino)phenol (819 mg, 3.38 mmol) was added cesium carbonate (918 mg, 2.82 mmol) followed by 4-(2-fluoropyridin-3-yl)cyclohexanol (220 mg, 1.127 mmol) as a solution in NMP (7.5 mL). The reaction mixture was heated to 200° C. for 2.5 h with microwave irradiation. The reaction mixture was diluted with water and extracted with 15% IPA:chloroform before drying over magnesium sulfate, filtering, and concentrating to a dark brown residue under reduced pressure.

Workup

  1. extractionextracted with 15% IPA
  2. dry with materialchloroform before drying over magnesium sulfate
  3. filtrationfiltering
  4. concentrationconcentrating to a dark brown residue under reduced pressure

Sources & evidence

ORD record
ord-9d0bebd32e8849519c7013f464dcf022
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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