4-(Benzyloxy)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline → 2-(6-(4-(Benzyloxy)quinolin-6-yl)pyridin-2-yl)thiazole

HRID 1028063Notes

Reaction equation

HRID 1028063 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.FC(F)(F)S(O[C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([C:40]2[S:41][CH:42]=[CH:43][N:44]=2)[N:35]=1)(=O)=O>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:34]3[N:35]=[C:36]([C:40]4[S:41][CH:42]=[CH:43][N:44]=4)[CH:37]=[CH:38][CH:39]=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 583876054-(Benzyloxy)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolineHCID 866564566-(Thiazol-2-yl)pyridin-2-yl trifluoromethanesulfonate

Product 1

HCID 583875912-(6-(4-(Benzyloxy)quinolin-6-yl)pyridin-2-yl)thiazoleYield 39%

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.), 6-(thiazol-2-yl)pyridin-2-yl trifluoromethanesulfonate (1.0 equiv.) and Pd(dppf)Cl2—CH2Cl2 (0.1 equiv.) in 3:1 DME/2M Na2CO3 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 (EtOAc eluant) to yield 2-(6-(4-(benzyloxy)quinolin-6-yl)pyridin-2-yl)thiazole (39%). LC/MS=396.0 (M+H), LC=3.34 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 (EtOAc eluant)

Sources & evidence

ORD record
ord-71f7fad8b0624bae85a14454e1367043
Source dataset
uspto-grants-2014_05
Patent number
US08735424B2

Reaction notes

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