Stannous chloride dihydrate → HCID 90413043, compound

HRID 930826Notes

Reaction equation

HRID 930826 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:12]=3[Cl:20])[N:10]=2)[CH:7]=1.O.O.Cl[Sn]Cl>C(O)C>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[C:15]([CH:14]=[CH:13][C:12]=3[Cl:20])[NH2:17])[N:10]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 90411524HCID 90411524, compound

Product 1

HCID 90413043HCID 90413043, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a suspension of 6-bromo-2-(2-chloro-5-nitrophenyl)imidazo[1,2-a]pyrimidine (1-3) (10 g, 28.28 mmol, 1.00 equiv) in ethanol (100 ml) was added SnCl2.2H2O (12.7 g) and stirred for 12 h at 75° C. The solvent was removed under vacuum and the residue was diluted with water. The pH value of the mixture was adjusted to 8-9 with sodium bicarbonate (sat.). The solids were collected by filtration and applied onto a silica gel column with ethyl acetate/petroleum ether (2/1) to give 2.6 g (28%) of 3-[6-bromoimidazo[1,2-a]pyrimidin-2-yl]-4-chloroaniline (1-4) as a light yellow solid. 1H-NMR: (d6-DMSO, 400 MHz): 9.37 (d, J=2.4 Hz, 1H), 8.63 (d, J=2.4 Hz, 1H), 8.47 (s, 1H), 7.56 (d, J=2.8 Hz, 1H), 7.18 (d, J=8.4 Hz, 1H), 6.59 (dd, J=8.4, 2.8 Hz, 1H), 5.44 (s, 2H). EI, m/z): MS (M+H)+=325

Workup

  1. customThe solvent was removed under vacuum
  2. additionthe residue was diluted with water
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-57855cd0e9e14b37b42a90f7b5d41ce0
Source dataset
uspto-grants-2016_03
Patent number
US09296754B2

Reaction notes

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