4-Toluenesulfonyl chloride → HCID 59191409, compound

HRID 626013Notes

Reaction equation

HRID 626013 reaction equation
[F:1][C:2]([F:22])([F:21])[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[N:13]=2)=[C:7]([O:19][CH3:20])[CH:6]=1)[OH:4].[S:23](Cl)([C:26]1[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=1)(=[O:25])=[O:24]>CN(C1C=CN=CC=1)C.ClCCl>[CH3:30][C:29]1[CH:31]=[CH:32][C:26]([S:23]([O:4][CH:3]([C:5]2[CH:10]=[CH:9][C:8]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[N:13]=3)=[C:7]([O:19][CH3:20])[CH:6]=2)[C:2]([F:1])([F:21])[F:22])(=[O:25])=[O:24])=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 59191306HCID 59191306, compound

Product 1

HCID 59191409HCID 59191409, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,2,2-trifluoro-1-{4-[(6-fluoropyridin-2-yl)oxy]-3-methoxyphenyl}ethanol (0.52 mmol; 165 mg), tosyl chloride (0.57 mmol; 109 mg) and DMAP (0.01 mmol; 1.5 mg) under argon in dichloromethane (4 mL) at 0° C. was added TEA (1.04 mmol; 145 μl). The reaction mixture was stirred at rt for 3 h, then washed with brine (2×), dried over MgSO4, concentrated and purified by preparative TLC on silica gel (ethyl acetate/cyclohexane—30/70) to yield the title compound (101 mg; 0.21 mmol; 41%).

Workup

  1. washwashed with brine (2×)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. custompurified by preparative TLC on silica gel (ethyl acetate/cyclohexane—30/70)

Sources & evidence

ORD record
ord-4fc8a9dc16a04b499e7e6da4a7609b96
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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