4-Bromo-2,6-dimethylphenol → HCID 69898859, compound

HRID 2308011Notes

Reaction equation

HRID 2308011 reaction equation
Cl[C:2]1[N:10]=[C:9]([CH3:11])[CH:8]=[C:7]([NH:12][CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[C:3]=1[C:4]([NH2:6])=[O:5].[CH3:18][C:19]1[CH:24]=[C:23]([Br:25])[CH:22]=[C:21]([CH3:26])[C:20]=1[OH:27].CC([O-])(C)C.[K+]>CN1C(=O)CCC1>[Br:25][C:23]1[CH:24]=[C:19]([CH3:18])[C:20]([O:27][C:2]2[N:10]=[C:9]([CH3:11])[CH:8]=[C:7]([NH:12][CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[C:3]=2[C:4]([NH2:6])=[O:5])=[C:21]([CH3:26])[CH:22]=1

Participants

5

Reactant 3

HCID 169194-Bromo-2,6-dimethylphenolHCID 23665647Potassium tert-butoxideHCID 86584333HCID 86584333, compound

Product 1

HCID 69898859HCID 69898859, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

To a mixture of 2-chloro-4-(1-ethyl-propylamino)-6-methyl-nicotinamide and 2,6-dimethyl-4-bromo-phenol in NMP was added t-BuOK. The resulting mixture was heated in a 160° C. oil bath overnight. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was separated, dried and concentrated, then purified through silica gel Biotage to give the title compound. 1H NMR(CDCl3) d 9.69(d,1H), 7.89(brs,1H), 7.20(s,2H), 6.13(s,1H), 5.5(brs,1H), 3.3(m,1H), 2.10(s,3H), 2.09(s,6H), 1.6(m,4H), 0.95(t,6H) ppm.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated
  6. custompurified through silica gel Biotage

Sources & evidence

ORD record
ord-1ab5f1ab35694250aa39855b90cae1b0
Source dataset
uspto-grants-2004_12
Patent number
US06833378B2

Reaction notes

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