Sodium Carbonate → HCID 86711467, compound

HRID 2274111Notes

Reaction equation

HRID 2274111 reaction equation
Br[C:2]1[C:3]([O:13][CH3:14])=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].[CH3:15][S:16]([C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[N:23][CH:24]=1)(=[O:18])=[O:17].C(=O)([O-])[O-].[Na+].[Na+]>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.O1CCOCC1>[Cl:9][C:6]1[C:7]([CH3:8])=[C:2]([C:21]2[CH:22]=[N:23][CH:24]=[C:19]([S:16]([CH3:15])(=[O:18])=[O:17])[CH:20]=2)[C:3]([O:13][CH3:14])=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 441193815-(Methylsulphonyl)pyridine-3-boronic acidHCID 866667591-(3-Bromo-5-chloro-2-methoxy-4-methylphenyl)ethanone

Product 1

HCID 86711467HCID 86711467, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Into a microwave vial was added 1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethanone (0.040 g, 0.14 mmol), [5-(methylsulfonyl)pyridin-3-yl]boronic acid (0.035 g, 0.17 mmol), 1.0 M sodium carbonate (0.35 mL, 0.35 mmol), 1,4-dioxane (0.87 mL) and tetrakis(triphenylphosphine)palladium(0) (0.010 g, 0.0086 mmol). The mixture was bubbled with N2 for 5 min, then heated at 100° C. overnight. The cooled reaction mixture was purified on silica gel to give the desired product (0.035 g, 71%). LCMS calculated for C16H17ClNO4S (M+H)+: m/z=354.1. found: 354.0.

Workup

  1. customThe mixture was bubbled with N2 for 5 min
  2. customThe cooled reaction mixture
  3. customwas purified on silica gel

Sources & evidence

ORD record
ord-f00c3a35f2f549a3b1ef7d84af2d4af8
Source dataset
uspto-grants-2015_09
Patent number
US09126948B2

Reaction notes

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