Dimethylformamide → 3-(1-{[2-Bromo-3',5'-bis(trifluoromethyl)biphenyl-4-yl]carbonyl}pyrrolidin-3-yl)pyridine

HRID 383774

Reaction equation

HRID 383774 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][C:3]=1[C:11]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[C:13]([C:21]([F:24])([F:23])[F:22])[CH:12]=1.CCN=C=N[CH2:30][CH2:31][CH2:32][N:33]([CH3:35])C.Cl.O[N:38]1[C:42]2[CH:43]=[CH:44][CH:45]=CC=2N=N1.[CH3:47]N(C=O)C>>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([N:38]2[CH2:45][CH2:44][CH:43]([C:47]3[CH:35]=[N:33][CH:32]=[CH:31][CH:30]=3)[CH2:42]2)=[O:10])[CH:5]=[CH:4][C:3]=1[C:11]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[C:13]([C:21]([F:24])([F:23])[F:22])[CH:12]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866577562-Bromo-3',5'-bis(trifluoromethyl)biphenyl-4-carboxylic acid

Product 1

HCID 866577533-(1-{[2-Bromo-3',5'-bis(trifluoromethyl)biphenyl-4-yl]carbonyl}pyrrolidin-3-yl)pyridine

Procedure

i-5d (179 mg, 1.21 mmol) was added to a stirred solution of 3a (500 mg, 1.21 mmol), N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (255 mg, 1.33 mmol) and 1-hydroxybenzotriazole 185 mg, 1.21 mmol) in DMF (8.00 mL). After 4 h, the reaction mixture was quenched with said, aq. NaHCO3 and extracted with EtOAc. The organic layer was washed with water and brine, dried (sodium sulfate) and concentrated in vacuo. The resulting crude residue was purified by column chromatography on silica gel (gradient elution; 0%-5% methanol/EtOAc as eluent) to afford the title compound 3b. m/z (ES) 543 (MH)+.

Workup

  1. customthe reaction mixture was quenched
  2. extractionaq. NaHCO3 and extracted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude residue was purified by column chromatography on silica gel (gradient elution; 0%-5% methanol/EtOAc as eluent)

Sources & evidence

ORD record
ord-565eb4acbea748179c320f971fd30d70
Source dataset
uspto-grants-2013_02
Patent number
US08367679B2

Linked notes

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