Sodium Carbonate → HCID 68291061, compound

HRID 2174547Notes

Reaction equation

HRID 2174547 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9](I)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C(=O)([O-])[O-:25].[Na+].[Na+]>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:3]([O:25][CH:20]([CH3:19])[CH3:15])([CH3:4])[CH3:8].[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]([C:18]2[CH:19]=[CH:20][C:15]([Br:14])=[CH:16][CH:17]=2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 79599(4-Bromophenyl)boronic acidHCID 10852539Methyl 2-amino-4-chloro-5-iodobenzoate2×

Product 2

HCID 7914Diisopropyl EtherHCID 68291061HCID 68291061, compoundYield 55.8%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of methyl 2-amino-4-chloro-5-iodobenzoate (Intermediate 2) (8.2 g, 26.3 mmol), (4-bromophenyl)boronic acid (5.29 g, 26.3 mmol), tetrakis(triphenylphosphine) palladium (0.304 g, 0.263 mmol) and sodium carbonate (79 mL, 1M in water, 79 mmol) in 1,4-dioxane (300 mL) was stirred 3 days at 80° C. After cooling, the mixture was filtered through celite, the filtrate was then diluted with water and extracted twice with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was triturated in diisopropylether, filtered and washed with acetonitrile then diisopropylether to give the title compound methyl 4-amino-4′-bromo-6-chloro-3-biphenylcarboxylate (2.5 g, 7.34 mmol, 27.9% yield) as an off-white powder. LCMS: (M+H)+=340-342; Rt=4.09 min.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered through celite
  3. additionthe filtrate was then diluted with water
  4. extractionextracted twice with dichloromethane
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated in diisopropylether
  9. filtrationfiltered
  10. washwashed with acetonitrile

Sources & evidence

ORD record
ord-9930b2bcb7194a1aa8a1ccf823270766
Source dataset
uspto-grants-2015_06
Patent number
US09061998B2

Reaction notes

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