Diisopropylethylamine → 4-(Benzyloxy)-6-(6-(2,6-difluorophenyl)pyridin-2-yl)quinoline

HRID 1028066Notes

Reaction equation

HRID 1028066 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21](Br)[N:20]=3)[CH:17]=2)[N:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:28]=1B(O)O.C(N(C(C)C)CC)(C)C>C1(C)C=CC=CC=1.C(O)C>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:28]4[C:27]([F:26])=[CH:32][CH:31]=[CH:30][C:29]=4[F:33])[N:20]=3)[CH:17]=2)[N:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27343362,6-Difluorophenylboronic acidHCID 583875984-(Benzyloxy)-6-(6-bromopyridin-2-yl)quinoline

Product 1

HCID 583875674-(Benzyloxy)-6-(6-(2,6-difluorophenyl)pyridin-2-yl)quinolineYield 74%

Reagents, catalysts & solvents 1

HCID 21863594Toluene ethanolSolvent

Procedure

A solution of 4-(benzyloxy)-6-(6-bromopyridin-2-yl)quinoline (1.0 equiv.), 2,6 difluorophenylboronic acid (3.0 equiv.), diisopropylethylamine (3.0 equiv) and tetrakis(triphenylphospine)palladium (0.1 equiv.) in 1:1 toluene/ethanol was heated in a microwave at 120° 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 (60-75 EtOAc/hexanes eluant) to yield 4-(benzyloxy)-6-(6-(2,6-difluorophenyl)pyridin-2-yl)quinoline (74%). LC/MS=425.1 (M+H), LC=3.59 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 (60-75 EtOAc/hexanes eluant)

Sources & evidence

ORD record
ord-240face549054277bf8b01839b413245
Source dataset
uspto-grants-2014_05
Patent number
US08735424B2

Reaction notes

Loading…