3,5-Difluorobenzylamine → HCID 37603177, compound

HRID 1921313Notes

Reaction equation

HRID 1921313 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH2:5][NH2:6].[Br:11][C:12]1[S:16][C:15]([C:17](Cl)=[O:18])=[CH:14][CH:13]=1>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH2:5][NH:6][C:17]([C:15]1[S:16][C:12]([Br:11])=[CH:13][CH:14]=1)=[O:18]

Participants

4

Reactant 2

HCID 1452113,5-DifluorobenzylamineHCID 6057125-Bromothiophene-2-carbonyl chloride

Product 1

HCID 37603177HCID 37603177, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Thionyl chloride (35 ml) is added dropwise to 5-bromo-2-thiophenecarboxylic acid (4.92 g, 23.77 mmol) at 0° C., and the mixture is then heated at 90° C. overnight. After the mixture has cooled to room temperature, the solvent is removed in vacuo, and the residue is washed with cold heptane. 5-Bromothiophene-2-carbonyl chloride is obtained as an almost white solid. 3,5-Difluorobenzylamine (209 mg, 1.46 mmol) is added to a mixture of 5-bromothiophene-2-carbonyl chloride (300 mg, 1.33 mmol), piperidinomethylpolystyrene (410 mg, 3.5 mmol/g, 1.44 mmol) in anhydrous dichloromethane (5 mL) and stirred for 2.5 hr. The reaction mixture is diluted with dichloromethane and filtered through silica gel. The filtrate is concentrated to afford 5-bromo-thiophene-2-carboxylic acid 3,5-difluoro-benzylamide as a white solid (400 mg, 90% yield).

Workup

  1. filtrationfiltered through silica gel
  2. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-6e5efe5c656343f2b6f71fa92ef247e6
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

Loading…