Tetrahydrofuran → Ethyl{7-[5-(2-methyl-propenyl)pyridin-2-yl]-7-azaspiro[3.5]non-2-yl}carbamate

HRID 336558Notes

Reaction equation

HRID 336558 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[NH:5][CH:6]1[CH2:9][C:8]2([CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18](Br)=[CH:17][N:16]=3)[CH2:11][CH2:10]2)[CH2:7]1)[CH3:2].O[C:24]([C:27](O)(C)C)([CH3:26])[CH3:25].CC(C)=CB([O-])[O-].C(=O)([O-])[O-].[Cs+].[Cs+].O1CCCC1>O>[CH2:1]([O:3][C:4](=[O:22])[NH:5][CH:6]1[CH2:9][C:8]2([CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([CH:25]=[C:24]([CH3:27])[CH3:26])=[CH:17][N:16]=3)[CH2:11][CH2:10]2)[CH2:7]1)[CH3:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 131731370Pinacol 2-methyl-1-propenylboronateHCID 131732015Ethyl[7-(5-bromopyridin-2-yl)-7-azaspiro[3.5]non-2-yl]carbamate

Product 1

HCID 131732014Ethyl{7-[5-(2-methyl-propenyl)pyridin-2-yl]-7-azaspiro[3.5]non-2-yl}carbamateYield 83.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The process is performed according to the method described in Example 2 (step 2.7.). Starting with 0.50 g (1.36 mmol) of ethyl[7-(5-bromopyridin-2-yl)-7-azaspiro[3.5]non-2-yl]carbamate, prepared in the preceding step, 0.33 mL (1.63 mmol) of pinacol 2-methyl-1-propenylboronate (commercial) and 1.33 g (4.07 mmol) of caesium carbonate, suspended in 9 mL of a 9/1 mixture of tetrahydrofuran and water, and 0.11 g (0.14 mmol) of PdCl2dppf.CH2Cl2, and after purifying on a column of silica gel, eluting with a 100/0/0 to 99/1/0.1 mixture of dichloromethane, methanol and 28% aqueous ammonia, 0.39 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 100/0/0 to 99/1/0.1 mixture of dichloromethane, methanol and 28% aqueous ammonia

Sources & evidence

ORD record
ord-cb3833f470064e05aef039b0038651d0
Source dataset
uspto-grants-2014_11
Patent number
US08889702B2

Reaction notes

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