Triethylamine → 2-Amino-5-bromopyridine-3-carboxamide

HRID 2201549Notes

Reaction equation

HRID 2201549 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4](O)=[O:5].C1C=CC2N(O)N=[N:18]C=2C=1.CCN=C=NCCCN(C)C.CCN(CC)CC.[NH4+].[Cl-]>CN(C=O)C>[NH2:1][C:2]1[N:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([NH2:18])=[O:5]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 7374452-Amino-5-bromonicotinic acid

Product 1

HCID 529879382-Amino-5-bromopyridine-3-carboxamideYield 90.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-amino-5-bromonicotinic acid (2.0 g, 9.20 mmol), HOBT (1.40 g, 11.2 mmol), EDCI (3.52 g, 18.4 mmol), Et3N (4.68 g, 46.0 mmol) and NH4Cl (2.48 g, 46.0 mmol) in DMF (100 mL) was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo, suspended in water and extracted with CH2Cl2. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give the product of 2-amino-5-bromonicotinamide (1.80 g, yield: 80%), which was used for the next step without further purification. 1H NMR (DMSO-d6, 400 MHz) δ 8.14 (dd, J=4.4 Hz, 2.4 Hz, 2H), 8.04 (s, 1H), 7.46 (s, 1H), 7.37 (s, 2H). MS (M+H)+: 216/218.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionextracted with CH2Cl2
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-753206cd7f57458d90f181ea24e9127c
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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