Potassium Carbonate → 4-[2-(3-tert-Butyl-phenylamino)-quinoxalin-6-yloxy]-pyridine-2-carboxylic Acid Methylamide

HRID 639366Notes

Reaction equation

HRID 639366 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]2[CH:21]=[N:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([OH:22])[CH:18]=3)[N:13]=2)[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:33][NH:34][C:35]([C:37]1[CH:42]=[C:41](Cl)[CH:40]=[CH:39][N:38]=1)=[O:36].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:33][NH:34][C:35]([C:37]1[CH:42]=[C:41]([O:22][C:17]2[CH:18]=[C:19]3[C:14](=[CH:15][CH:16]=2)[N:13]=[C:12]([NH:11][C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=2)[CH:21]=[N:20]3)[CH:40]=[CH:39][N:38]=1)=[O:36]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14768144-Chloro-N-methylpicolinamideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 1361450542-(3-tert-Butyl-phenylamino)-quinoxalin-6-ol

Product 1

HCID 117506994-[2-(3-tert-Butyl-phenylamino)-quinoxalin-6-yloxy]-pyridine-2-carboxylic Acid Methylamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture containing 2-(3-tert-butyl-phenylamino)-quinoxalin-6-ol (1 eq), potassiumbis(trimethylsilyl)amide (4eq), was stirred in dimethylformamide for 30 min. at room temperature. To this mixture was added 4-chloro-pyridine-2-carboxylic acid methylamide (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
  2. customat 170° C
  3. concentrationThe reaction mixture was then concentrated
  4. custompartitioned between ethyl acetate and water
  5. customThe organic layer was separated
  6. washwashed with brine
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification on Prep LC

Sources & evidence

ORD record
ord-56526b2e1b914cc5982377d356bb5195
Source dataset
uspto-grants-2010_04
Patent number
US07691866B2

Reaction notes

Loading…