Acetic Acid → HCID 15956112, compound

HRID 1474004Notes

Reaction equation

HRID 1474004 reaction equation
[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]

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 10796Cesium carbonateHCID 12534286(2-Methylcyclopentyl)methanolHCID 860960062-Chloro-5-(thiazol-2-ylamino)phenol

Product 1

HCID 15956112HCID 15956112, compoundYield 3.6%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 8003PentaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  1. washthe reaction mixture was washed with brine, saturated aqueous NaHCO3
  2. dry with materialdried over MgSO4
  3. filtrationfiltered with Et2O
  4. waitAfter 4 h
  5. washwashed with 5% aqueous NaOH solution and brine
  6. dry with materialThe organic phase was dried over Na2SO4
  7. concentrationconcentrated
  8. customthe crude product was purified by flash chromatography on silica gel (hexane:EtOAc 8/2)

Sources & evidence

ORD record
ord-86238a36c46340649ad200a1827a8bbe
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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