Cesium carbonate → HCID 86688553, compound

HRID 1617318Notes

Reaction equation

HRID 1617318 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][CH3:10])=[N:6][CH:7]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH:22]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[C:11]([O:15][C:16]([N:18]1[CH2:19][CH:20]=[C:21]([C:2]2[CH:7]=[N:6][C:5]([O:8][CH2:9][CH3:10])=[CH:4][CH:3]=2)[CH2:22][CH2:23]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 8172375-Bromo-2-ethoxypyridineHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate

Product 1

HCID 86688553HCID 86688553, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Under inert gas atmosphere 5.00 g (23.3 mmol) 5-bromo-2-ethoxy-pyridine are added to a mixture of 7.19 g (23.3 mmol) 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester, 95 mg (1.2 mmol) PdCl2(dppf)xCH2Cl2 and 15.2 g (46.5 mol) Cs2CO3 in 50 mL DMF and 10 mL H2O. The mixture is stirred for 12 h at 80° C. After that time, the solvent is evaporated, the residue taken up in DCM and washed with brine. After drying over sodium sulphate, the solvent is removed in vacuo and the residue is purified by column chromatography (silica gel; gradient PE/EtOAc 20:1→10:1) to yield the desired product which was directly used in the next step.

Workup

  1. customAfter that time, the solvent is evaporated
  2. washwashed with brine
  3. dry with materialAfter drying over sodium sulphate
  4. customthe solvent is removed in vacuo
  5. customthe residue is purified by column chromatography (silica gel; gradient PE/EtOAc 20:1→10:1)

Sources & evidence

ORD record
ord-03eb61481f974094a146b8c045a93e71
Source dataset
uspto-grants-2014_07
Patent number
US08765959B2

Reaction notes

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