Water → HCID 86702525, compound

HRID 877048Notes

Reaction equation

HRID 877048 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH:10]=1)=[N:8][N:7]1[C:11](Cl)=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:13]([Cl:15])=[N:14][C:6]=21.O.O1CCCC1.[Cl-].[NH4+]>C(O)C.[Zn]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH:10]=1)=[N:8][N:7]1[CH:11]=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:13]([Cl:15])=[N:14][C:6]=21

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 86702526HCID 86702526, compound

Product 1

HCID 86702525HCID 86702525, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

7 g (17.8 mmol) 8-Bromo-2,4-dichloro-3-phenylpyrimido[1,2-b]indazole were suspended in a mixture of 453 mL ethanol, 322 mL water and 173 mL tetrahydrofuran. After addition of 4.5 g (84.4 mmol) ammonium chloride and 7.5 g (114 mmol) zinc the mixture was stirred over night at room temperature. The mixture was filtered via a glass fibre filter, washed with THF and the organic solvents were removed. The residue was treated with a mixture of water and ethyl acetate and the organic phase was separated. The aqueous phase was extracted twice with ethyl acetate and the combined organic extracts were evaporated without prior drying because the product had already precipitated. 3.7 g (57.9%) of the title compound were isolated.

Workup

  1. filtrationThe mixture was filtered via a glass fibre
  2. filtrationfilter
  3. washwashed with THF
  4. customthe organic solvents were removed
  5. additionThe residue was treated with a mixture of water and ethyl acetate
  6. customthe organic phase was separated
  7. extractionThe aqueous phase was extracted twice with ethyl acetate
  8. customthe combined organic extracts were evaporated
  9. customwithout prior drying because the product
  10. customhad already precipitated

Sources & evidence

ORD record
ord-21feb802e5a74091861f384e2bdd1a3c
Source dataset
uspto-grants-2015_03
Patent number
US08987286B2

Reaction notes

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