Diethyl Ether → 2-(2-Bromophenyl)-6-chloro-3-[(phenylmethyl)oxy]pyridine

HRID 269586Notes

Reaction equation

HRID 269586 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](I)[C:5]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].C(OCC)C>C1(C)C=CC=CC=1.C(O)C.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.O>[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:6]1[C:5]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=[C:2]([Cl:1])[N:7]=1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 2773294(2-Bromophenyl)boronic acidHCID 587310103-(Benzyloxy)-6-chloro-2-iodopyridine

Product 1

HCID 587310032-(2-Bromophenyl)-6-chloro-3-[(phenylmethyl)oxy]pyridineYield 82.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 21863594Toluene ethanolSolvent

Conditions

Temperature
90 °C

Procedure

6-Chloro-2-iodo-3-[(phenylmethyl)oxy]pyridine (346 mg, 1 mmol) and 2-bromophenylboronic acid (201 mg, 1 mmol) were dissolved in 1:1 toluene/ethanol (10 ml) and potassium carbonate (1.1 g, 8 mmol) and tetrakis(triphenylphosphine)palladium(0) (116 mg, 0.1 mmol) added. The mixture was stirred under nitrogen and heated at 90° C. for 2 hours. After cooling, diethyl ether and water were added and the organic layer washed with water, dried (MgSO4) and evaporated. The yellow oil was flash chromatographed, eluting with 2-10% ethyl acetate/isohexane to give the title compound as a clear oil (308 mg) LC/MS t=3.77, [MH+] 376, 378.

Workup

  1. additionadded
  2. temperatureAfter cooling
  3. washthe organic layer washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customchromatographed
  7. washeluting with 2-10% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-91f679d38be445ccb4bd5b207bc58cd8
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Reaction notes

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