Diisopropylethylamine → HCID 59408785, compound

HRID 1188114Notes

Reaction equation

HRID 1188114 reaction equation
[I-].ClC1C=CC=C[N+]=1C.CCN(C(C)C)C(C)C.[NH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][N:21]=1.[Br:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](O)=[O:36])=[CH:33][N:32]=1>C1COCC1>[Br:30][C:31]1[CH:39]=[CH:38][C:34]([C:35]([NH:19][C:20]2[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][N:21]=2)=[O:36])=[CH:33][N:32]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 2389326-Bromonicotinic acidHCID 737487Methyl 6-aminonicotinate

Product 1

HCID 59408785HCID 59408785, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Chloro-1-methylpyridinium iodide (2.2 g, 9.8 mmol) and DIPEA (1 ml) were added to a mixture of 5-fluoropyridin-2-amine 1 (554 mg, 4.9 mmol) and 6-bromonicotinic acid 2 (1 g, 4.9 mmol) in THF. The reaction mixture was stirred at rt for 2 days. At the conclusion of the reaction, the reaction mixture was concentrated to ⅓ of its volume and the precipitated product was filtered off. The filtrate was concentrated, diluted with chloroform (100 ml), washed with water and brine and then dried over Na2SO4. Evaporation of the solvent gave a crude yellow product, which crystallized in EtOAc to give 6-bromo-N-(5-fluoropyridin-2-yl)nicotinamide 3 (1.05 g, 71%) as a white solid. Mp. 173-174° C.

Workup

  1. customAt the conclusion of the reaction
  2. concentrationthe reaction mixture was concentrated
  3. filtrationthe precipitated product was filtered off
  4. concentrationThe filtrate was concentrated
  5. additiondiluted with chloroform (100 ml)
  6. washwashed with water and brine
  7. dry with materialdried over Na2SO4
  8. customEvaporation of the solvent
  9. customgave a crude yellow product, which
  10. customcrystallized in EtOAc

Sources & evidence

ORD record
ord-a54b1df480034e39a2a484be7cb43f5c
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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