Stannous chloride dihydrate → HCID 61676010, compound

HRID 589804Notes

Reaction equation

HRID 589804 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[NH:10][C:9]([C:11]3[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:12]=3[Cl:20])=[N:8][C:5]2=[N:6][CH:7]=1.O.O.Cl[Sn]Cl>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[NH:10][C:9]([C:11]3[CH:16]=[C:15]([CH:14]=[CH:13][C:12]=3[Cl:20])[NH2:17])=[N:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 90450868HCID 90450868, compound

Product 1

HCID 61676010HCID 61676010, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 6-bromo-2-(2-chloro-5-nitrophenyl)-1H-imidazo[4,5-b]pyridine I-2a (18 g, 50.91 mmol, 1.00 equiv) in ethanol (200 mL) was added SnCl2.2H2O (17.3 g, 76.55 mmol, 1.50 equiv) and heated to reflux overnight. The resulting mixture was concentrated under vacuum and the residue was diluted with 200 mL of H2O. The pH value of the mixture was adjusted to 8 with sodium carbonate (sat.). A filtration was performed and the solids were applied on a silica gel column and eluted with ethyl acetate/PE (1/1) to give 12 g (73%) of 3-[6-bromo-1H-imidazo[4,5-b]pyridin-2-yl]-4-chloroaniline (I-2b) as a yellow solid. 1H-NMR (DMSO, 400 MHz): 13.00-13.53 (m, 1H), 8.46 (s, 1H), 8.30 (brs, 1H), 7.26 (d, J=8.4 Hz, 1H), 7.05 (brs, 1H), 6.76 (dd, J=8.4, 2.8 Hz, 1H), 5.57 (brs, 2H). MS M/Z=325 (M+1).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. additionthe residue was diluted with 200 mL of H2O
  5. filtrationA filtration
  6. washeluted with ethyl acetate/PE (1/1)

Sources & evidence

ORD record
ord-ee511a73c745436d8f97816350f222e2
Source dataset
uspto-grants-2016_01
Patent number
US09233961B2

Reaction notes

Loading…