Stannous chloride dihydrate → HCID 57955331, compound

HRID 73673Notes

Reaction equation

HRID 73673 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=2)=[C:8]2[N:13]([C:14]=1[Br:15])[N:12]=[CH:11][N:10]=[C:9]2[NH2:16])=[O:5])[CH3:2].O.O.[Sn](Cl)Cl>CCO>[NH2:16][C:9]1[C:8]2=[C:7]([C:17]3[CH:18]=[CH:19][C:20]([NH2:23])=[CH:21][CH:22]=3)[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:14]([Br:15])[N:13]2[N:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 57955233Ethyl 4-amino-7-bromo-5-(4-nitrophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate

Product 1

HCID 57955331HCID 57955331, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl-4-amino-7-bromo-5-(4-nitrophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate (2.06 g, 5.07 mmol) was suspended in EtOH (30 mL) and treated with tin(II)chloride dihydrate (3.66 g. 16.2 mmol). The mixture was heated to reflux for 18 h. The mixture was concentrated then diluted with EtOAc and saturated NaHCO3 solution. The emulsion was filtered and the filtrate was transferred to a separatory funnel. The organic layer was washed with water and saturated NaCl solution, dried then (MgSO4) and concentrated to afford 1.5 g of the desired product as tan solid (79%). 1H-NMR (DMSO-d6) δ 8.00 (s, 1H), 7.00 (d, J=8.6, 1H), 6.62 (d, J=9.2, 3H), 5.40 (bd, 2H), 5.19 (bs, 2H), 4.05 (q, J=7.0, 2H), 1.03 (t, J=7.0, 3H); MS [M+H]+=376.0, 378.0; LCMS RT=2.02.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 18 h
  3. concentrationThe mixture was concentrated
  4. additionthen diluted with EtOAc and saturated NaHCO3 solution
  5. filtrationThe emulsion was filtered
  6. customthe filtrate was transferred to a separatory funnel
  7. washThe organic layer was washed with water and saturated NaCl solution
  8. customdried
  9. concentration(MgSO4) and concentrated

Sources & evidence

ORD record
ord-d09a96c1d337449c866fb2f4b3140c56
Source dataset
uspto-grants-2014_09
Patent number
US08829185B2

Reaction notes

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