Sodium Carbonate → HCID 11282074, compound

HRID 1991370Notes

Reaction equation

HRID 1991370 reaction equation
Br[C:2]1[C:3]([CH3:26])=[C:4]([C:18]([OH:25])=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:20]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=1[Cl:17])=[O:6].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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>[Cl:17][C:9]1[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:8]=1[NH:7][C:5]([C:4]1[C:3]([CH3:26])=[C:2]([C:2]2[CH:3]=[CH:4][CH:18]=[CH:19][CH:20]=2)[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:18]=1[OH:25])=[O:6]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 57438078HCID 57438078, compound

Product 1

HCID 11282074HCID 11282074, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-Bromo-5-tert-butyl-N-(2-chloro-4-nitro-phenyl)-6-hydroxy-2-methyl-benzamide (0.18 g, 0.4 mmole) in dioxane (5 ml) under nitrogen phenylboronic acid (50.0 mg, 0.4 mmole), tetrakis(triphenylphosphine)palladium(0) (10 mg, 0.009 mmole) and sodium carbonate (1.41 ml, 2 M solution in water) were added. The reaction mixture was heated at 100° C. for 6 hours. The reaction mixture was evaporated, diluted with ethyl acetate and the organic phase was washed with citric acid solution (10%). The organic phase was dried over sodium sulphate and evaporated. The crude compound was purified by column chromatography.

Workup

  1. customThe reaction mixture was evaporated
  2. additiondiluted with ethyl acetate
  3. washthe organic phase was washed with citric acid solution (10%)
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. customevaporated
  6. customThe crude compound was purified by column chromatography

Sources & evidence

ORD record
ord-4f228187c10849a2aa2d1c61f5c59630
Source dataset
uspto-grants-2010_01
Patent number
US07645791B2

Reaction notes

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