Potassium Carbonate → HCID 59401299, compound

HRID 2060867Notes

Reaction equation

HRID 2060867 reaction equation
[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[OH:13].[F:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1F)[C:18]#[N:19].C([O-])([O-])=O.[K+].[K+]>C1CS(=O)(=O)CC1>[F:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[O:13][C:8]1[C:9]2[C:4](=[C:3]([CH2:2][OH:1])[CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1)[C:18]#[N:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5872033,4-DifluorobenzonitrileHCID 57979480HCID 57979480, compound

Product 1

HCID 59401299HCID 59401299, compound

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-hydroxymethylnaphthalen-1-ol (Preparation 32) (350 mg, 2.01 mmol) and 3,4-difluorobenzonitrile (279 mg, 2.01 mmol) in sulfalone (8 mL) was added K2CO3 (1.39 g, 10.05 mmol) and the mixture heated to 80° C. for 16 h before cooling to rt. The mixture was partitioned between water (50 mL) and EtOAc (3×50 mL), the organic phase was washed with water (3×50 mL), brine (50 mL) and dried (MgSO4). Solvent was removed in vacuo and the residue purified by column chromatography (SiO2, MeOH:DCM, 2:98) to give the title compound: RT=3.54 min; m/z (ES+)=276.1 [M H2O]+.

Workup

  1. temperaturebefore cooling to rt
  2. customThe mixture was partitioned between water (50 mL) and EtOAc (3×50 mL)
  3. washthe organic phase was washed with water (3×50 mL), brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. customSolvent was removed in vacuo
  6. customthe residue purified by column chromatography (SiO2, MeOH:DCM, 2:98)

Sources & evidence

ORD record
ord-b0e2d07ca3e24ad286840dbafde97452
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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