Potassium Carbonate → HCID 86689169, compound

HRID 1752498Notes

Reaction equation

HRID 1752498 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[N:6][C:7]=1[Cl:8].C([O-])([O-])=O.[K+].[K+].[F:16][CH2:17]I.[NH4+].[Cl-]>C(#N)C.CCOC(C)=O>[Cl:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([O:9][CH2:17][F:16])=[CH:5][N:6]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 13981373Fluoro(iodo)methaneHCID 143916722,3-Dichloro-5-hydroxypyridine

Product 1

HCID 86689169HCID 86689169, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5,6-dichloro-pyridin-3-ol [11860-92-9] (500 mg, 3.05 mmol) and K2CO3 (632 mg, 4.57 mmol) in dry ACN (12 ml) was added fluoro-iodomethane (1.156 ml, 9.15 mmol) at 0° C. The light yellow suspension was stirred for 5 min at 0° C. and then heated up to 120° C. for 30 min. Saturated aq. NH4Cl was added, followed by EtOAc. The organic layer was separated and the aqueous layer was extracted twice with EtOAc. The combined organic layers were washed with brine, dried with Na2SO4, filtered and evaporated to give a brown oil. The crude material was directly used in the next step without further purification.

Workup

  1. temperatureheated up to 120° C. for 30 min
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted twice with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customto give a brown oil
  9. customThe crude material was directly used in the next step without further purification

Sources & evidence

ORD record
ord-5d3803863bda469dac70d93e221b8515
Source dataset
uspto-grants-2015_10
Patent number
US09163011B2

Reaction notes

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