Potassium Carbonate → Methyl 4-amino-2'-bromo-2-biphenylcarboxylate

HRID 269564Notes

Reaction equation

HRID 269564 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.[NH2:11][C:12]1[CH:13]=[CH:14][C:15](Br)=[C:16]([CH:21]=1)[C:17]([O:19][CH3:20])=[O:18].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1.C(O)C>C(OCC)C.O.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>[NH2:11][C:12]1[CH:21]=[C:16]([C:17]([O:19][CH3:20])=[O:18])[C:15]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 245495Methyl 5-amino-2-bromobenzoateHCID 2773294(2-Bromophenyl)boronic acidHCID 21863594Toluene ethanol

Product 1

HCID 58730987Methyl 4-amino-2'-bromo-2-biphenylcarboxylate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-bromophenyl boronic acid (600 mg, 3.0 mmol), methyl 5-amino-2-bromobenzoate (1.5 g, 6.5 mmol), potassium carbonate (2.07 g, 15 mmol) and tetrakis(triphenylphosphine)palladium (0) (345 mg, 5 mol %) in 1:1 toluene/ethanol (20 ml) was stirred and heated at 90° C. under nitrogen for 12 hours. After cooling the mixture was diluted with diethyl ether and water and the organic phase dried (MgSO4) and evaporated to dryness. The residue was chromatographed with dichloromethane/iso-hexane (1:2->1:1) to yield the title compound as a pale yellow gum. (682 mg, 74%).

Workup

  1. temperatureAfter cooling the mixture
  2. dry with materialthe organic phase dried (MgSO4)
  3. customevaporated to dryness
  4. customThe residue was chromatographed with dichloromethane/iso-hexane (1:2->1:1)

Sources & evidence

ORD record
ord-273f753770b94019aec781ec869b4b74
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Reaction notes

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