Dimethyl Sulfoxide → 2-{3-[(2,2-Difluoro-2-phenylethyl)amino]-6-chloro-2-fluorophenyl}ethanal

HRID 2184193Notes

Reaction equation

HRID 2184193 reaction equation
CS(C)=O.CCN(C(C)C)C(C)C.[F:14][C:15]([F:35])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:16][NH:17][C:18]1[C:19]([F:28])=[C:20]([CH2:25][CH2:26][OH:27])[C:21]([Cl:24])=[CH:22][CH:23]=1>C(Cl)Cl>[F:35][C:15]([F:14])([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH2:16][NH:17][C:18]1[C:19]([F:28])=[C:20]([CH2:25][CH:26]=[O:27])[C:21]([Cl:24])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 224753362-{3-[(2,2-Difluoro-2-phenylethyl)amino]-6-chloro-2-fluorophenyl}ethanol

Product 1

HCID 224753142-{3-[(2,2-Difluoro-2-phenylethyl)amino]-6-chloro-2-fluorophenyl}ethanalYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of DMSO (1.03 mL, 14.5 mmol), DIEA (1.99 mL, 11.4 mmol), and 2-{3-[(2,2-difluoro-2-phenylethyl)amino]-6-chloro-2-fluorophenyl}ethanol (1.45 g, 4.4 mmol), as prepared according to the procedure in the preceding step, in DCM (140 mL) in an ice-bath was added sulfur trioxide pyridine complex (1.82 g, 11.4 mmol) and stirred at the same temperature for 3.5 hours. The mixture was diluted with DCM (300 mL), washed with 10% citric acid (3 times), H2O, and brine, dried over Na2SO4, and concentrated to give the title compound (1.43 g, 99% yield) as an orange oil, that was used without further purification.

Workup

  1. additionwas added sulfur trioxide pyridine complex (1.82 g, 11.4 mmol)
  2. washwashed with 10% citric acid (3 times), H2O, and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f6c9ed1ce53c4b48a85c3bcf7c2f5bc1
Source dataset
uspto-grants-2005_05
Patent number
US06900231B2

Reaction notes

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