Potassium Carbonate → HCID 67960030, compound

HRID 527535Notes

Reaction equation

HRID 527535 reaction equation
[CH3:1][CH:2]([C:4]1[C:8]2=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=[C:7]2[O:6][N:5]=1)[CH3:3].CC(C1OC2C(=C(O)C=CC=2)N=1)C.Cl[C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][N:29]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:3][CH:2]([C:4]1[C:8]2[C:9]([O:13][C:28]3[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][N:29]=3)=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][N:5]=1)[CH3:1]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 59589221HCID 59589221, compound2×HCID 136378656HCID 136378656, compound

Product 1

HCID 67960030HCID 67960030, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3-(1-methylethyl)-1,2-benzisoxazol-4-ol and 2-(1-methylethyl)-1,3-benzoxazol-4-ol (Intermediate 40, 13 mg), was dissolved in DMF (2.0 mL) and 2-chloro-5-nitropyridine (11.6 mg, 0.073 mmol) was added, followed by potassium carbonate (30 mg, 0.22 mmol). The reaction mixture was heated under microwave irradiation at 110° C. for 1 hour. After the removal of the volatiles, the residue obtained was charged on a silica gel column (Biotage SP1 system) and eluted with Cyhexane/EtOAc (from 10/0 to 9/1, then 9/1, then from 9/1 to 8/2) to afford the title compound (8.7 mg).

Workup

  1. customAfter the removal of the volatiles
  2. customthe residue obtained
  3. additionwas charged on a silica gel column (Biotage SP1 system)
  4. washeluted with Cyhexane/EtOAc (from 10/0 to 9/1

Sources & evidence

ORD record
ord-0d1cc9f14ac04510935b952b6a3ac6a5
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

Loading…