Water → HCID 86702522, compound

HRID 877046Notes

Reaction equation

HRID 877046 reaction equation
[Cl:1][C:2]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:14](Cl)[N:5]2[N:6]=[C:7]3[C:12]([CH:11]=[C:10]([F:13])[CH:9]=[CH:8]3)=[C:4]2[N:3]=1.O.O1CCCC1.[Cl-].[NH4+]>C(O)C.[Zn]>[Cl:1][C:2]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][N:5]2[N:6]=[C:7]3[C:12]([CH:11]=[C:10]([F:13])[CH:9]=[CH:8]3)=[C:4]2[N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 867025232,4-Dichloro-9-fluoro-3-phenylpyrimido[1,2-b]indazole

Product 1

HCID 86702522HCID 86702522, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

7.2 g (21.7 mmol) 2,4-Dichloro-9-fluoro-3-phenylpyrimido[1,2-b]indazole were suspended in a mixture of 551 mL ethanol, 392 mL water and 211 mL tetrahydrofuran. After addition of 5.5 g (102.7 mmol) ammonium chloride and 9.1 g (138.7 mmol) zinc the mixture was stirred over night at room temperature. The mixture was filtered via a glass fibre filter, and the organic solvents were removed. The product which precipitated was filtered off (3.4 g=51.9%). 3.4 g (42.2%) of the starting material wereregained by stirring the zinc slurry with 1 L ethyl acetate, filtration of the zinc via a glass fibre filter and evaporation of the organic solvent. The product was contaminated with 9-fluoro-3-phenylpyrimido[1,2-b]indazole (25%).

Workup

  1. filtrationThe mixture was filtered via a glass fibre
  2. filtrationfilter
  3. customthe organic solvents were removed
  4. customThe product which precipitated
  5. filtrationwas filtered off (3.4 g=51.9%)
  6. stirringby stirring the zinc slurry
  7. filtrationwith 1 L ethyl acetate, filtration of the zinc via a glass fibre
  8. filtrationfilter
  9. customevaporation of the organic solvent

Sources & evidence

ORD record
ord-ed60992be9334b41b52f0c8bebd78bd3
Source dataset
uspto-grants-2015_03
Patent number
US08987286B2

Reaction notes

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