Sodium Carbonate → Ethyl 2-(2-(6-cyclopropylpyridin-3-yl)phenylthio)-2-methylpropanoate

HRID 1503094Notes

Reaction equation

HRID 1503094 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]([CH3:14])([CH3:13])[C:10]([O-:12])=[O:11].[CH:15]1([C:18]2[N:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=2)[CH2:17][CH2:16]1.C(=O)([O-])[O-].[Na+].[Na+].O1CCO[CH2:35][CH2:34]1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:15]1([C:18]2[N:23]=[CH:22][C:21]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[S:8][C:9]([CH3:14])([CH3:13])[C:10]([O:12][CH2:34][CH3:35])=[O:11])=[CH:20][CH:19]=2)[CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 422050782-(2-Bromophenylthio)-2-methylpropanoateHCID 53338917(6-Cyclopropylpyridin-3-yl)boronic acid

Product 1

HCID 54764233Ethyl 2-(2-(6-cyclopropylpyridin-3-yl)phenylthio)-2-methylpropanoate

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(2-bromophenylthio)-2-methylpropanoate (1 eq), 6-cyclopropylpyridin-3-ylboronic acid (1 eq), aqueous sodium carbonate solution (2 M, 4 eq), and Pd(PPh3)4 (0.05 eq) in dioxane is degassed. The mixture is sealed, heated at 80° C., washed with water, extracted with ethyl acetate, dried (MgSO4), concentrated and purified by chromatography.

Workup

  1. customis degassed
  2. customThe mixture is sealed
  3. washwashed with water
  4. extractionextracted with ethyl acetate
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. custompurified by chromatography

Sources & evidence

ORD record
ord-3d4bb93312c04d8f83f445f70242ea35
Source dataset
uspto-grants-2015_12
Patent number
US09212135B2

Reaction notes

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