Tetrahydrofuran → Ethyl {2-[5'-(2-methylpropenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]ethyl}carbamate

HRID 1019699Notes

Reaction equation

HRID 1019699 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][NH:16][C:17](=[O:21])[O:18][CH2:19][CH3:20])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.O[C:23]([C:26](O)(C)C)([CH3:25])[CH3:24].CC(C)=CB([O-])[O-].C(=O)([O-])[O-].[Cs+].[Cs+].O1CCCC1>O>[CH3:25][C:23]([CH3:26])=[CH:24][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][NH:16][C:17](=[O:21])[O:18][CH2:19][CH3:20])[CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 86661342Ethyl [2-(5'-bromo-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)ethyl]carbamateHCID 131731370Pinacol 2-methyl-1-propenylboronate

Product 1

HCID 86661343Ethyl {2-[5'-(2-methylpropenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]ethyl}carbamateYield 80.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The process is performed according to the method described in Example 10 (step 10.5.). Starting with 1.00 g (2.81 mmol) of ethyl [2-(5′-bromo-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)ethyl]carbamate, prepared in the preceding step, 0.61 g (3.37 mmol) of pinacol 2-methyl-1-propenylboronate (commercial), 2.74 g (8.42 mmol) of caesium carbonate, suspended in 18 mL of a 9/1 mixture of tetrahydrofuran and water, and 0.23 g (0.28 mmol) of PdCl2dppf.CH2Cl2, and after purifying on a column of silica gel, eluting with a 99/1/0.1 mixture of dichloromethane, methanol and 28% aqueous ammonia, 0.75 g of expected product is obtained in the form of a wax.

Workup

  1. customCH2Cl2, and after purifying on a column of silica gel
  2. washeluting with a 99/1/0.1 mixture of dichloromethane, methanol and 28% aqueous ammonia

Sources & evidence

ORD record
ord-f92c0d2e5c8b4e6e9ddfbba224d324f0
Source dataset
uspto-grants-2014_05
Patent number
US08716289B2

Reaction notes

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