2-Amino-5-bromopyridine → HCID 59408778, compound

HRID 1188102Notes

Reaction equation

HRID 1188102 reaction equation
[I-].ClC1C=CC=C[N+]=1C.[Br:10][C:11]1[CH:28]=[CH:27][C:14]([C:15]([NH:17][C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][N:19]=2)=[O:16])=[CH:13][N:12]=1.[NH2:29][C:30]1[CH:35]=[CH:34][C:33]([Br:36])=[CH:32][N:31]=1.CCN(C(C)C)C(C)C>C1COCC1>[Br:10][C:11]1[CH:28]=[CH:27][C:14]([C:15]([NH:17][C:18]2[CH:26]=[CH:25][C:21]([C:22](=[O:24])[NH:29][C:30]3[CH:35]=[CH:34][C:33]([Br:36])=[CH:32][N:31]=3)=[CH:20][N:19]=2)=[O:16])=[CH:13][N:12]=1

Participants

6

Reactant 4

HCID 706222-Amino-5-bromopyridineHCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 59408766HCID 59408766, compound

Product 1

HCID 59408778HCID 59408778, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-chloro-1-methylpyridinium iodide (2.37 g, 18.6 mmol) was added to a suspension of 6-(6-bromonicotinamido)nicotinic acid 4 (2 g, 6.21 mmol) and 2-amino-5-bromopyridine 5 (1.07 g, 6.21 mmol) in THF (100 ml), followed by DIPEA (2.4 g, 18.6 mmol). The reaction mixture was stirred for 4 days at RT. The suspension was filtered off and washed with water (25 ml). The filtrate was concentrated, diluted in chloroform, washed with water and brine, and then dried over Na2SO4. The product precipitated during evaporation and was dried under vacuum to give 6-bromo-N-(5-(5-bromopyridin-2-ylcarbamoyl)pyridin-2-yl)nicotinamide 6 as a yellow solid (400 mg, 14%). Mp. 245-247° C.

Workup

  1. filtrationThe suspension was filtered off
  2. washwashed with water (25 ml)
  3. concentrationThe filtrate was concentrated
  4. additiondiluted in chloroform
  5. washwashed with water and brine
  6. dry with materialdried over Na2SO4
  7. customThe product precipitated during evaporation
  8. customwas dried under vacuum

Sources & evidence

ORD record
ord-adf2ee4239ea4076845a19186f22f520
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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