Dimethylformamide → [8-Fluoro-2-isopropyl-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-yloxy]acetic acid methyl ester

HRID 1922151Notes

Reaction equation

HRID 1922151 reaction equation
[F:1][C:2]1[C:11]2[N:10]=[C:9]([CH:12]([CH3:14])[CH3:13])[C:8]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[CH:25][CH:24]=[N:23]4)=[CH:18][CH:17]=3)=[C:7]([CH3:27])[C:6]=2[C:5]([OH:28])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Br[CH2:41][C:42]([O:44][CH3:45])=[O:43]>[Cl-].[NH4+].O>[CH3:45][O:44][C:42](=[O:43])[CH2:41][O:28][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[C:11]2[C:6]=1[C:7]([CH3:27])=[C:8]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]3[CH:26]=[CH:25][CH:24]=[N:23]3)=[CH:18][CH:17]=1)[C:9]([CH:12]([CH3:13])[CH3:14])=[N:10]2

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 1363309328-Fluoro-2-isopropyl-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-ol

Product 1

HCID 67456367[8-Fluoro-2-isopropyl-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-yloxy]acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A mixture of 8-fluoro-2-isopropyl-4-methyl-3-(4-pyrazol-1-yl-benzyl)quinolin-5-ol (0.066 g), potassium carbonate (0.073 g) and N,N-dimethylformamide (0.35 mL) was treated with methyl bromoacetate (0.020 mL), and the resulting mixture was stirred at room temperature for 12 hours. The mixture was diluted with saturated aqueous ammonium chloride solution (3.0 mL) and water (20 mL), and extracted with ethyl acetate (3×5 mL). The combined extracts were washed with water (2.0 mL) and saturated aqueous sodium chloride solution (2.0 mL), and dried over magnesium sulfate. Purification of the residue by column chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (1:0 to 1:1 by volume) gave title compound as a colourless oil (0.079 g).

Workup

  1. extractionextracted with ethyl acetate (3×5 mL)
  2. washThe combined extracts were washed with water (2.0 mL) and saturated aqueous sodium chloride solution (2.0 mL)
  3. dry with materialdried over magnesium sulfate
  4. customPurification of the residue by column chromatography on silica gel
  5. washeluting with a mixture of cyclohexane and ethyl acetate (1:0 to 1:1 by volume)

Sources & evidence

ORD record
ord-4938ef64957e4f8cb1082ba0bb076ec6
Source dataset
uspto-grants-2012_05
Patent number
US08173812B2

Reaction notes

Loading…