3-Aminopyridine → HCID 82547286, compound

HRID 1056270Notes

Reaction equation

HRID 1056270 reaction equation
[NH2:1][C:2]1[C:10]([Br:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.CCN(C(C)C)C(C)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.C([O-])(O)=O.[Na+]>CCOC(C)=O>[NH2:1][C:2]1[C:10]([Br:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)=[O:6]

Participants

7

Reactant 5

HCID 100093-AminopyridineHCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 2702592-Amino-3-bromobenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 82547286HCID 82547286, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 2-amino-3-bromobenzoic acid (Aldrich; 2.00 g, 9.26 mmol) and 3-aminopyridine (Aldrich; 0.871 g, 9.26 mmol) in 10 mL EtOAc was added DIPEA (1.93 mL, 11.11 mmol) followed by 1-propanephosphonic acid cyclic anhydride (T3P) (50 wt. % solution in EtOAc; Matrix Scientific; 6.00 mL, 10.18 mmol). The reaction became warm and after 5 min a thick precipitate formed. The reaction was stirred overnight. The reaction was treated with sat'd aq. NaHCO3 and EtOAc. The organic layer was washed 1× sat'd aq. NaHCO3, 1× brine, dried over Na2SO4, filtered, and concentrated in vacuo to give 2-amino-3-bromo-N-(pyridin-3-yl)benzamide (2.13, 7.29 mmol, 79% yield) as a yellow solid used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.37 (1H, s), 8.87 (1H, d, J=2.2 Hz), 8.31 (1H, dd, J=4.6, 1.5 Hz), 8.08-8.14 (1H, m), 7.71 (1H, dd, J=7.8, 1.4 Hz), 7.62 (1H, dd, J=7.8, 1.4 Hz), 7.39 (1H, dd, J=8.2, 4.7 Hz), 6.57-6.71 (1H, m), 6.36 (2H, s). m/z (ESI, +ve) 291.9/293.9 (M+H)+.

Workup

  1. temperatureThe reaction became warm and after 5 min a thick precipitate
  2. customformed
  3. washThe organic layer was washed 1×
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2211d77c84a74154a2f8b14987a1fb1b
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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