Sodium Carbonate → HCID 10732886, compound

HRID 2121238Notes

Reaction equation

HRID 2121238 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][O:21][C:22](=[O:35])[C:23]1[CH:32]=[C:31](Br)[C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][C:24]=1[NH2:34].[CH3:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>CCOCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)C>[CH3:30][O:29][C:27](=[O:28])[C:26]1[CH:25]=[C:24]([NH2:34])[C:23]([C:22]([O:21][CH3:20])=[O:35])=[CH:32][C:31]=1[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=1[CH3:36]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27332672-Methylphenyl boronic acidHCID 23436066Dimethyl 2-amino-5-bromobenzene-1,4-dicarboxylate

Product 1

HCID 10732886HCID 10732886, compoundYield 83.1%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of palladium acetate (260 mg, 1.16 mmol) and triphenylphosphine (1.21 g, 4.63 mmol) was stirred for 10 minutes at ambient temperature and then the product of Example 319A (11.1 g, 38.6 mmol), 2-methylphenylboronic acid (5.77 g, 42.4 mmol), ethanol (18 mL) and aqueous 2M sodium carbonate (157 mL) were added. The reaction mixture was warmed to reflux and stirred for 18 hours. The reaction mixture was cooled to ambient temperature and diluted with ether. The aqueous phase was extracted with ether. The combined organic layers were washed with water, dried, filtered and concentrated in vacuo to give an orange oil. Chromatography on silica gel (25% ethyl acetate-hexanes) gave the desired compound (9.6 g, 83%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was warmed
  2. temperatureto reflux
  3. extractionThe aqueous phase was extracted with ether
  4. washThe combined organic layers were washed with water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give an orange oil

Sources & evidence

ORD record
ord-ff3ed8de33154b2a8f5208bb3fe4235f
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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