Diisopropylethylamine → HCID 86670804, compound

HRID 878246Notes

Reaction equation

HRID 878246 reaction equation
[F:1][CH:2]([F:18])[CH2:3][NH:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17].[CH3:19][S:20]([C:23]1[CH:24]=[C:25]([CH:43]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:45]=1)[C:26](N(C)C1C=NC=CC=1C1C=CC=CC=1C)=[O:27])(=[O:22])=[O:21].F[B-](F)(F)F.BrC1C=CC=C[N+]=1CC.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[F:18][CH:2]([F:1])[CH2:3][N:4]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])[C:26](=[O:27])[C:25]1[CH:43]=[C:44]([C:46]([F:49])([F:47])[F:48])[CH:45]=[C:23]([S:20]([CH3:19])(=[O:22])=[O:21])[CH:24]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27363002-Bromo-1-ethylpyridinium tetrafluoroborateHCID 601978053-Methanesulfonyl-N-methyl-N-(4-o-tolyl-pyridin-3-yl)-5-trifluoromethyl-benzamideHCID 86670767HCID 86670767, compound

Product 1

HCID 86670804HCID 86670804, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2,2-difluoroethyl)-4-(2-fluorophenyl)pyridin-3-amine (112 mg, 444 μmol) in CH2Cl2 (3 mL) was added 3-(methylsulfonyl)-5-(trifluoromethyl)benzoic acid (119 mg, 444 μmol, example 114, intermediate) and 2-bromo-1-ethylpyridinium tetrafluoroborate (146 mg, 533 μmol) and N,N-diisopropylethylamine (115 mg, 155 μL, 888 μmol). The reaction mixture was stirred at room temperature for 24 hours and then concentrated under vacuum. The residue was dissolved in 30 mL 1M aqueous HCl and 30 mL EtOAc and the layers were separated. The aqueous layer was extracted a second time with 30 mL EtOAc. The organic layers were washed with 30 mL 1M aqueous HCl and 30 mL 10% aqueous NaHCO3 solution and 30 mL brine, dried over MgSO4, filtered and concentrated under vacuum. Yellow solid (84 mg, 38%). MS (ESI): m/z=503.085 [M+H]+.

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe residue was dissolved in 30 mL 1M aqueous HCl
  3. custom30 mL EtOAc and the layers were separated
  4. extractionThe aqueous layer was extracted a second time with 30 mL EtOAc
  5. washThe organic layers were washed with 30 mL 1M aqueous HCl and 30 mL 10% aqueous NaHCO3 solution and 30 mL brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7793cfbcde6d4872992ecd5c25fd9b14
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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