Potassium Hydroxide → HCID 67047543, compound

HRID 606890Notes

Reaction equation

HRID 606890 reaction equation
O.O.[Sn](Cl)Cl.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:16]=[N:17][CH:18]=[C:19]([O:21][CH3:22])[CH:20]=2)=[CH:9][C:8]=1[N+:23]([O-])=O.[OH-].[K+]>C(O)C.O1CCCC1>[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:16]=[N:17][CH:18]=[C:19]([O:21][CH3:22])[CH:20]=2)=[CH:9][C:8]=1[NH2:23]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 61436Stannous chloride dihydrateHCID 67047850HCID 67047850, compound

Product 1

HCID 67047543HCID 67047543, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Add tin (II) chloride dihydrate (1.41 g, 6.26 mmol) to a suspension of 3-(4-fluoro-3-nitrophenylethynyl)-5-methoxypyridine, (prepared as described in EXAMPLE 116), (190 mg, 0.69 mmol) in ethanol (20 mL) and tetrahydrofuran (17 mL) under nitrogen and heat at 70° C. for 2 h. Cool the reaction mixture, add a 50% aqueous solution of potassium hydroxide (100 mL), and extract with diethyl ether (2×100 mL). Wash the combined organic phases with an aqueous saturated solution of sodium chloride (100 mL), dry (sodium sulfate), filter, and concentrate. Purify the residue by silica gel chromatography, eluting with ethyl acetate to give the title compound as a yellow solid. Further purify the title compound by silica gel chromatography, eluting with 100% dichloromethane to 20:80 ethyl acetate:dichloromethane, to give the title compound as a white solid (143 mg, 86%).

Workup

  1. temperatureCool the reaction mixture
  2. extractionextract with diethyl ether (2×100 mL)
  3. washWash the combined organic phases with an aqueous saturated solution of sodium chloride (100 mL)
  4. dry with materialdry (sodium sulfate)
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the residue by silica gel chromatography
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-6d12d1019ec64ec9b2fabc6d3c43900f
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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