(Diethylamino)sulfur trifluoride → HCID 59191387, compound

HRID 626016Notes

Reaction equation

HRID 626016 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)O.CCN(S(F)(F)[F:29])CC>ClCCl>[F:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([O:11][C:8]2[CH:9]=[CH:10][C:5]([CH:3]([F:29])[C:2]([F:22])([F:21])[F:1])=[CH:6][C:7]=2[O:19][CH3:20])[N:13]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 59191306HCID 59191306, compound

Product 1

HCID 59191387HCID 59191387, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,2,2-trifluoro-1-{4-[(6-fluoropyridin-2-yl)oxy]-3-methoxyphenyl}ethanol (0.22 mmol; 70 mg) under argon in dichloromethane (2 mL) at −78° C. was added dropwise DAST (0.22 mmol; 29 μl). The reaction mixture was let come back to rt for 2 h and quenched with brine (3 ml). The aqueous phase was collected, neutralized with sodium bicarbonate and extracted twice with chloroform. The organic phases were combined, dried over MgSO4, concentrated and purified by preparative TLC on silica gel (ethyl acetate/cyclohexane—30/70) to yield the title compound (25 mg; 0.08 mmol; 37%).

Workup

  1. customquenched with brine (3 ml)
  2. customThe aqueous phase was collected
  3. extractionextracted twice with chloroform
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. custompurified by preparative TLC on silica gel (ethyl acetate/cyclohexane—30/70)

Sources & evidence

ORD record
ord-4f3d74769d8f401e990f8e4f02eb33f2
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

Loading…