Ammonia → HCID 67234620, compound

HRID 2377579Notes

Reaction equation

HRID 2377579 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].N.Cl.[CH3:12][N:13](C)C(=O)C>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Zn].[C-]#N.[Zn+2].[C-]#N>[C:12]([C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9])#[N:13]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 31374DimethylacetamideHCID 404247372-Chloro-3-fluoro-5-hydroxypyridine

Product 1

HCID 67234620HCID 67234620, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst

Conditions

Temperature
140 °C

Procedure

A mixture of 2.94 g (20 mmol) of 6-chloro-5-fluoro-3-pyridinol, 360 mg (0.4 mmol) of tris(benzylideneacetone)dipalladium(0), 440 mg (0.8 mmol) 1,1′-bis(diphenylphosphino)ferrocene, 156 mg (2.4 mmol) of zinc powder and 1.4 g (12 mmol) of zinc cyanide in 40 ml of N,N-dimethylacetamide is prepared and the reaction mixture is then stirred at 140° C. for 5 hours. It is left to stand overnight at room temperature. 40 ml of 2 N aqueous ammonia are added slowly and the pH is then adjusted to about 4.5 with 5 N hydrochloric acid. The mixture is extracted 3 times with 100 ml of ethyl acetate and the organic phase obtained is dried over magnesium sulfate and concentrated under reduced pressure. The evaporation residue is purified by chromatography on silica gel using a methylcyclohexane/ethyl acetate mixture (in a gradient of 8/2 to 5/5; v/v) as the eluent to give 1.8 g of the expected compound in the form of an orange oil (yield=67%).

Workup

  1. customis prepared
  2. waitIt is left
  3. waitto stand overnight at room temperature
  4. extractionThe mixture is extracted 3 times with 100 ml of ethyl acetate
  5. customthe organic phase obtained
  6. dry with materialis dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe evaporation residue is purified by chromatography on silica gel using a methylcyclohexane/ethyl acetate mixture (in a gradient of 8/2 to 5/5

Sources & evidence

ORD record
ord-b8a6c6dd0033435e9bdfe73761aa5d08
Source dataset
uspto-grants-2008_12
Patent number
US07470671B2

Reaction notes

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