Potassium Carbonate → HCID 59254861, compound

HRID 639363Notes

Reaction equation

HRID 639363 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([OH:19])[CH:15]=3)[N:10]=2)=[CH:4][C:3]=1[CH3:20].C[Si]([N-][Si](C)(C)C)(C)C.[K+].Cl[C:32]1[CH:37]=[CH:36][N:35]=[C:34]([C:38]([NH:40][CH3:41])=[O:39])[CH:33]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19][C:32]4[CH:37]=[CH:36][N:35]=[C:34]([C:38]([NH:40][CH3:41])=[O:39])[CH:33]=4)[CH:15]=3)[N:10]=2)=[CH:4][C:3]=1[CH3:20]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14768144-Chloro-N-methylpicolinamideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 59254888HCID 59254888, compound

Product 1

HCID 59254861HCID 59254861, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture of 2-[(4-bromo-3-methylphenyl)amino]quinolin-6-ol and potassium bis(trimethylsilyl)amide (2 eq), was stirred in dimethylformamide for 30 min at room temperature. To this mixture was added (4-chloro(2-pyridyl)-N-methylcarboxamide (1 eq) and potassium carbonate (1.2 eq) and microwaved for 6 mins at 170° C. The reaction mixture was then concentrated and partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, dried, filtered and concentrated. Purification on Prep LC yielded the desired product.

Workup

  1. custommicrowaved for 6 mins at 170° C
  2. concentrationThe reaction mixture was then concentrated
  3. custompartitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. washwashed with brine
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification on Prep LC

Sources & evidence

ORD record
ord-692ea5a789114f7f839a861db6537e1f
Source dataset
uspto-grants-2010_04
Patent number
US07691866B2

Reaction notes

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