Water → Benzenesulfonic acid 3-chloro-4-(3,3,3-trifluoro-2-hydroxy-1-methyl-2-quinolin-3-yl-propyl)-phenyl ester

HRID 333840Notes

Reaction equation

HRID 333840 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:26])[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:25])[C:9]([OH:24])([C:14]1[CH:15]=[N:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]([F:13])([F:12])[F:11].C(=O)([O-])[O-].[Cs+].[Cs+].[C:33]1([S:39](Cl)(=[O:41])=[O:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.O>CN(C)C(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([O:26][S:39]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)(=[O:41])=[O:40])[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:25])[C:9]([OH:24])([C:14]1[CH:15]=[N:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]([F:11])([F:13])[F:12]

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chloride2×HCID 10796Cesium carbonateHCID 574212993-Chloro-4-(3,3,3-trifluoro-2-hydroxy-1-methyl-2-quinolin-3-yl-propyl)-phenol

Product 1

HCID 57449969Benzenesulfonic acid 3-chloro-4-(3,3,3-trifluoro-2-hydroxy-1-methyl-2-quinolin-3-yl-propyl)-phenyl esterYield 39.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a suspension of 3-chloro-4-(3,3,3-trifluoro-2-hydroxy-1-methyl-2-quinolin-3-yl-propyl)-phenol (Example 179, 55 mg) and cesium carbonate (52 mg) in N,N-dimethylacetamide (1 ml) was added benzenesulfonyl chloride (25 mg). After being stirred at room temperature for 2 days, more benzenesulfonyl chloride (14 mg) was added and the mixture was stirred at room temperature for 2 h. Water was added and the mixture was extracted with EtOAc. The organic phase was washed with brine and with water and dried (MgSO4). The product was purified by chromatography (SiO2, cyclohexane=>cyclohexane/EtOAc 1:1) to give the title compound (29 mg) as an off-white solid. MS (m/e)=522.2 [M+H+].

Workup

  1. stirringthe mixture was stirred at room temperature for 2 h
  2. extractionthe mixture was extracted with EtOAc
  3. washThe organic phase was washed with brine and with water
  4. dry with materialdried (MgSO4)
  5. customThe product was purified by chromatography (SiO2, cyclohexane=>cyclohexane/EtOAc 1:1)

Sources & evidence

ORD record
ord-e5936d8953db43a6a7cbcac964a8dc18
Source dataset
uspto-grants-2014_11
Patent number
US08883786B2

Reaction notes

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