Sodium Carbonate → Ethyl 2-methyl-2-(2-(pyridin-4-yl)phenylthio)propanoate

HRID 1503097Notes

Reaction equation

HRID 1503097 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].[N:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCO[CH2:32][CH2:31]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>[CH3:13][C:9]([S:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:18]1[CH:19]=[CH:20][N:15]=[CH:16][CH:17]=1)([CH3:14])[C:10]([O:12][CH2:31][CH3:32])=[O:11]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 2734379(Pyridin-4-yl)boronic acidHCID 422050782-(2-Bromophenylthio)-2-methylpropanoate

Product 1

HCID 68000733Ethyl 2-methyl-2-(2-(pyridin-4-yl)phenylthio)propanoate

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(2-bromophenylthio)-2-methylpropanoate (1 eq), pyridin-4-ylboronic acid (leq), 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-9dff4d44968d4476a0e3206bb6cf453d
Source dataset
uspto-grants-2015_12
Patent number
US09212135B2

Reaction notes

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