Pyridine → HCID 90451417, compound

HRID 589807Notes

Reaction equation

HRID 589807 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[NH:10][C:9]([C:11]3[CH:12]=[C:13]([CH:15]=[CH:16][C:17]=3[Cl:18])[NH2:14])=[N:8][C:5]2=[N:6][CH:7]=1.N1C=CC=CC=1.Cl[C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[NH:10][C:9]([C:11]3[CH:12]=[C:13]([NH:14][C:26](=[O:27])[O:28][CH:29]([CH3:31])[CH3:30])[CH:15]=[CH:16][C:17]=3[Cl:18])=[N:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7917Isopropyl chloroformateHCID 61676010HCID 61676010, compound

Product 1

HCID 90451417HCID 90451417, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3-[6-bromo-1H-imidazo[4,5-b]pyridin-2-yl]-4-chloroaniline (I-2b) (1 g, 3.08 mmol, 1.00 equiv) in DMF (10 mL) at 0° C. was added 0.5 ml of pyridine followed by isopropyl chloroformate (solution 1M in toluene) (3.85 ml, 3.85 mmol, 1.25 equiv). The reaction mixture was stirred overnight at room temperature and then quenched by the addition of water. The resulting mixture was extracted with ethyl acetate and the combined organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by flash chromatography (0 to 100% Ethyl acetate/Hexanes) to afford the title compound I-11. 1H NMR (400 MHz, DMSO) δ 9.95 (s, 1H), 8.49 (s, 1H), 8.34 (s, 1H), 8.02 (s, 1H), 7.63 (s, 1H), 7.57 (d, J=8.8, 1H), 4.97 4.80 (m, 1H), 1.26 (d, J=6.2, 6H); MS M/Z=409.0 (M+1). RT=1.77: Method B.

Workup

  1. customquenched by the addition of water
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washthe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash chromatography (0 to 100% Ethyl acetate/Hexanes)

Sources & evidence

ORD record
ord-f0e4241e1dc841ae9ed8f2fc80cea61a
Source dataset
uspto-grants-2016_01
Patent number
US09233961B2

Reaction notes

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