Cesium carbonate → {3-[(4-Chloro-benzyl)-(1-methyl-1H-pyrazole-3-sulfonyl)-amino]-phenoxy}-acetic acid tert-butyl ester

HRID 386487Notes

Reaction equation

HRID 386487 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[Cl:10][C:11]1[CH:34]=[CH:33][C:14]([CH2:15][N:16]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=2)[S:17]([C:20]2[CH:24]=[CH:23][N:22]([CH3:25])[N:21]=2)(=[O:19])=[O:18])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[C:6]([O:5][C:3](=[O:4])[CH2:2][O:32][C:28]1[CH:29]=[CH:30][CH:31]=[C:26]([N:16]([CH2:15][C:14]2[CH:13]=[CH:12][C:11]([Cl:10])=[CH:34][CH:33]=2)[S:17]([C:20]2[CH:24]=[CH:23][N:22]([CH3:25])[N:21]=2)(=[O:19])=[O:18])[CH:27]=1)([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 672303441-Methyl-1H-pyrazole-3-sulfonic acid (4-chloro-benzyl)-(3-hydroxy-phenyl)-amide

Product 1

HCID 67231689{3-[(4-Chloro-benzyl)-(1-methyl-1H-pyrazole-3-sulfonyl)-amino]-phenoxy}-acetic acid tert-butyl esterYield 82.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl bromoacetate (87.3 μl, 0.596 mmol) was added to a stirred solution of 1-methyl-1H-pyrazole-3-sulfonic acid (4-chloro-benzyl)-(3-hydroxy-phenyl)-amide (150 mg, 0.40 mmol) and cesium carbonate (388 mg, 1.19 mmol) in anhydrous dimethyl formamide (10 ml) and then stirred at ambient for 16 hours. The reaction was diluted with ethyl acetate (10 ml), washed with water (3×20 ml) and the organic extracts were concentrated in vacuo to obtain crude product. The residue was purified by flash chromatography eluting with 10% methanol/dichloromethane to yield a yellow oil (163 mg, 56% yield). HPLC retention time 6.47 min Mass spectrum (ES+) m/z 509 (M+H).

Workup

  1. washwashed with water (3×20 ml)
  2. concentrationthe organic extracts were concentrated in vacuo
  3. customto obtain crude product
  4. customThe residue was purified by flash chromatography
  5. washeluting with 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-b3a26504d338437396a64002a2ef55f1
Source dataset
uspto-grants-2013_02
Patent number
US08372840B2

Reaction notes

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