Potassium Carbonate → HCID 66669893, compound

HRID 1517895Notes

Reaction equation

HRID 1517895 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([OH:21])=[C:16]([O:19][CH3:20])[CH:17]=2)[N:12]=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:37][CH2:38][CH2:39][OH:40]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:28])[CH3:27])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH2:37][CH2:38][CH2:39][OH:40])=[C:16]([O:19][CH3:20])[CH:17]=2)[N:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 136346386HCID 136346386, compound

Product 1

HCID 66669893HCID 66669893, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 3-fluoro-4-(7-hydroxy-6-methoxyquinolin-4-yloxy)phenylcarbamate (400 mg, 1 mmol) in DMF (4 mL) was added K2CO3 (276 mg, 2 mmol) and 3-bromopropan-1-ol (154 mg, 1.1 mmol). The reaction was stirred at rt overnight. The solvent was removed, and the residue was partitioned between water (10 mL) and CH2Cl2 (20 mL). The organic layer was separated, dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAC to 10% methanol in EtOAC) to give the title compound as a light yellow solid (300 mg, 65%).

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between water (10 mL) and CH2Cl2 (20 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography (EtOAC to 10% methanol in EtOAC)

Sources & evidence

ORD record
ord-95356119a9104eaeb2cb2f8043479bac
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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