Triethylamine → 5-bromo-N-(2-fluoro-ethyl)-nicotinamide

HRID 1867513Notes

Reaction equation

HRID 1867513 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[F:11][CH2:12][CH2:13][NH2:14].CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([NH:14][CH2:13][CH2:12][F:11])=[O:9]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 99962-FluoroethylamineHCID 887075-Bromonicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 860043575-bromo-N-(2-fluoro-ethyl)-nicotinamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2.03 g (10 mmol) 5-bromonicotinic acid, 1 g (1 eq.) 2-fluoroethylamine, 2.31 g (1.2 eq.) EDC.HCl, 123 mg (0.1 eq.) DMAP and 5.6 mL (4 eq.) triethylamine are stirred in 60 mL dichloromethane for 20 hours at room temperature. The reaction mixture is extracted with dichloromethane and water, the combined organic phases are washed with brine, dried with sodium sulfate and evaporated. The residue is triturated in diethylether and hexane to yield after filtration the desired product as a white powder. MS(ES+): 347 and 349 (M+1).

Workup

  1. extractionThe reaction mixture is extracted with dichloromethane and water
  2. washthe combined organic phases are washed with brine
  3. dry with materialdried with sodium sulfate
  4. customevaporated
  5. customThe residue is triturated in diethylether
  6. customhexane to yield
  7. filtrationafter filtration the desired product as a white powder

Sources & evidence

ORD record
ord-9febcbfd0ee645548d8d0226a2435ac9
Source dataset
uspto-grants-2009_12
Patent number
US07632851B2

Reaction notes

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