[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][OH:8].Br.CC(O)=O.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]2[S:23][CH:24]=[CH:25][N:26]=2)=[CH:17][C:16]=1O.C([O-])([O-])=O.[Cs+].[Cs+]>CCCCC.CC(C)=O.CCOC(C)=O>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([NH:21][C:22]2[S:23][CH:24]=[CH:25][N:26]=2)=[CH:19][C:20]=1[O:8][CH2:7][C:3]1[CH2:4][CH2:5][CH2:6][C:2]=1[CH3:1]
To a solution of (2-methylcyclopent-1-yl)methanol (29 mg, 0.26 mmol) in pentane (0.7 mL) at 0° C. was added 45% HBr in AcOH (0.07 mL, 0.52 mmol). After having been stirred for 30 min, the reaction mixture was washed with brine, saturated aqueous NaHCO3, dried over MgSO4 and filtered with Et2O. This solution was added to a solution of 2-chloro-5-(thiazol-2-ylamino)phenol (59 mg, 0.26 mmol) and Cs2CO3 (85 mg, 0.26 mmol) in acetone (1 mL). After 4 h, the reaction mixture was diluted with AcOEt and washed with 5% aqueous NaOH solution and brine. The organic phase was dried over Na2SO4, concentrated and the crude product was purified by flash chromatography on silica gel (hexane:EtOAc 8/2) to give the product (3 mg, 3% yield).
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