Trimethyl orthoformate → HCID 67778750, compound

HRID 1039068Notes

Reaction equation

HRID 1039068 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[N-:9]=[N+:10]=[N-:11].[Na+].[CH3:13]OC(OC)OC>C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:13]=[N:11][N:10]=[N:9]2)=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 33557Sodium AzideHCID 8194405-Amino-2-fluoropyridine

Product 1

HCID 67778750HCID 67778750, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6-fluoropyridin-3-amine (1.12 g, 10 mmol), sodium azide (0.98 g, 15 mmol) and trimethylorthoformate (1.7 g, 16 mmol) were added to acetic acid (20 mL), and stirred at room temperature over night. The reaction was heated to 120° C. reflux for 7 hours. The reaction was cooled down to room temperature, poured into ice water (50 mL), extracted with ethyl acetate (50 mL), second wash with sodium hydroxide (1N, 20 mL). The organic phase was dried by magnesium sulfate, filtered, concentrated and purified by column chromatography through a 80 gram Analogix™ silica gel cartridge eluting with 50% ethyl acetate/hexanes to give the title compound as a white solid.

Workup

  1. temperatureThe reaction was heated to 120° C.
  2. temperaturereflux for 7 hours
  3. temperatureThe reaction was cooled down to room temperature
  4. extractionextracted with ethyl acetate (50 mL)
  5. washsecond wash with sodium hydroxide (1N, 20 mL)
  6. dry with materialThe organic phase was dried by magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by column chromatography through a 80 gram Analogix™ silica gel cartridge
  10. washeluting with 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-edb4ec191a5742b7a179652b8278bb48
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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