Potassium Carbonate → 4-(2-(4-bromophenylamino)benzo[d]oxazol-5-yloxy)-N-methylpicolinamide

HRID 2070259Notes

Reaction equation

HRID 2070259 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[O:10][C:11]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:12]=3[N:13]=2)=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].Cl[C:30]1[CH:35]=[CH:34][N:33]=[C:32]([C:36]([NH:38][CH3:39])=[O:37])[CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[O:10][C:11]3[CH:17]=[CH:16][C:15]([O:18][C:30]4[CH:35]=[CH:34][N:33]=[C:32]([C:36]([NH:38][CH3:39])=[O:37])[CH:31]=4)=[CH:14][C:12]=3[N:13]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14768144-Chloro-N-methylpicolinamideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 220403872-[(4-Bromophenyl)amino]benzoxazol-5-ol

Product 1

HCID 545817304-(2-(4-bromophenylamino)benzo[d]oxazol-5-yloxy)-N-methylpicolinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture containing 2-[(4-bromophenyl)amino]benzoxazol-5-ol (1 eq), potassium bis(trimethylsilyl)amide (4 eq), was stirred in dimethylformamide for 30 min at room temperature. To this mixture was added (4-chloro(2-pyridyl)-N-methyl-carboxamide (1 eq) and Potassium carbonate (1.2 eq) and microwaved for 6 mins at 150° 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. MS: MH+=439.

Workup

  1. custommicrowaved for 6 mins at 150° 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-1feae02b7d834f73b4d6d0475c018eee
Source dataset
uspto-grants-2012_10
Patent number
US08299108B2

Reaction notes

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