2,6-Dibromopyridine → 4-(Benzyloxy)-6-(6-bromopyridin-2-yl)quinoline

HRID 1028065Notes

Reaction equation

HRID 1028065 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16](B3OC(C)(C)C(C)(C)O3)[CH:17]=2)[N:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31](Br)[N:30]=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.COCCOC>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:31]3[CH:32]=[CH:33][CH:34]=[C:29]([Br:28])[N:30]=3)[CH:17]=2)[N:12]=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 122742,6-DibromopyridineHCID 583876054-(Benzyloxy)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline

Product 1

HCID 583875984-(Benzyloxy)-6-(6-bromopyridin-2-yl)quinolineYield 36%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 4-(benzyloxy)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (1.0 equiv.), 2,6 dibromopyridine (1.0 equiv.) and Pd(dppf)Cl2—CH2Cl2 (0.1 equiv.) in 3:1 DME/2M Na2CO3 was heated in a microwave at 100° C. for 20 minutes. Upon cooling, the solution was partitioned between EtOAc and H2O. Upon separation, the organic layer was washed with NaCl(sat.), dried over MgSO4, concentrated and purified by silica gel chromatography (70-90 EtOAc/hexanes eluant) to yield 4-(benzyloxy)-6-(6-bromopyridin-2-yl)quinoline (36%). LC/MS=391.1/393.1 (M+H), LC=3.36 min.

Workup

  1. temperatureUpon cooling
  2. customthe solution was partitioned between EtOAc and H2O
  3. customUpon separation
  4. washthe organic layer was washed with NaCl(sat.)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography (70-90 EtOAc/hexanes eluant)

Sources & evidence

ORD record
ord-d06e05df8eb54070b3bb3b6979c81e73
Source dataset
uspto-grants-2014_05
Patent number
US08735424B2

Reaction notes

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