Dimethyl Sulfoxide → HCID 59730256, compound

HRID 492568Notes

Reaction equation

HRID 492568 reaction equation
[F:1][C:2]1[C:16]([F:17])=[C:15]([CH:18]=[O:19])[CH:14]=[CH:13][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][N:6]=1.C([O-])([O-])=[O:21].[K+].[K+].CS(C)=O>O>[F:1][C:2]1[C:16]([F:17])=[C:15]([CH:18]=[O:19])[CH:14]=[CH:13][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]([NH2:10])=[O:21])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 59730380HCID 59730380, compound

Product 1

HCID 59730256HCID 59730256, compoundYield 148.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add 30% aq. B202 (7.95 ml) to a suspension of 6-(2,3-difluoro-4-formyl-phenoxy)-nicotinonitrile (2.07 g, 7.95 mmol), K2CO3 (550 mg, 3.98 mmol) and DMSO (20 ml) stirring in an ice/water bath. After one hour, pour the reaction mixture into water and extract with EtOAc. Wash the extract with water and brine before drying (MgSO4) and concentrating to give 6-(2,3-difluoro-4-formyl-phenoxy)-nicotinamide (1.64 g) as a white solid. 1HNMR (DMSO-d6): 10.14 (s, 1H), 8.58 (s, 1H), 8.33 (d, 1H), 8.07 (s, 1H), 7.74 (t, 1H), 7.55 (s, 1H), 7.33 (d, 1H), 7.27 (t, 1H).

Workup

  1. additionAdd 30% aq. B202 (7.95 ml)
  2. extractionextract with EtOAc
  3. washWash the
  4. extractionextract with water and brine
  5. dry with materialbefore drying (MgSO4)
  6. concentrationconcentrating

Sources & evidence

ORD record
ord-ac16a0aacd1e4e0dbd71520af2833c5c
Source dataset
uspto-grants-2009_05
Patent number
US07531557B2

Reaction notes

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