Cesium carbonate → HCID 58547684, compound

HRID 454879

Reaction equation

HRID 454879 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:14][CH:13]([OH:15])[CH2:12]1.C([O-])([O-])=O.[Cs+].[Cs+].[Br:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][C:28]=1Cl>CN(C=O)C.O>[Br:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][C:28]=1[O:15][CH:13]1[CH2:12][N:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)[CH2:14]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 8176963-Bromo-4-chloropyridineHCID 58547721HCID 58547721, compound

Product 1

HCID 58547684HCID 58547684, compoundYield 61.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-(quinolin-2-yl)azetidin-3-ol (see PREPARATION P1.2, step 1; 320 mg, 1.60 mmol) in DMF (10 mL) was added Cs2CO3 (1.04 g, 3.2 mmol) and 3-bromo-4-chloropyridine (307 mg, 1.60 mmol). The mixture was stirred at 90° C. overnight and then diluted with water (20 mL) and extracted with EtOAc (2×30 mL). The combined organic extracts were washed with water (30 mL) and brine (30 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (5% to 30% EtOAc in petroleum ether) to give the title product (350 mg, 0.98 mmol, 61% yield) as white solid. ESI-MS (M+1): 356 calc. for C17H14BrN3O 355.

Workup

  1. extractionextracted with EtOAc (2×30 mL)
  2. washThe combined organic extracts were washed with water (30 mL) and brine (30 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by flash column chromatography on silica gel (5% to 30% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-19efdbaebc044124addd1d073d33e0e3
Source dataset
uspto-grants-2013_07
Patent number
US08497265B2

Linked notes

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