Tetrahydrofuran → 7-[5-(4-Fluorophenyl)pyridin-2-yl]-7-azaspiro[3.5]nonan-2-ol

HRID 336536Notes

Reaction equation

HRID 336536 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:17][CH2:16][C:11]3([CH2:14][CH:13]([OH:15])[CH2:12]3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[F:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O1CCCC1>C(Cl)Cl.O>[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[CH:3]=[CH:4][C:5]([N:8]3[CH2:17][CH2:16][C:11]4([CH2:14][CH:13]([OH:15])[CH2:12]4)[CH2:10][CH2:9]3)=[N:6][CH:7]=2)=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 2856454-Fluorophenylboronic acidHCID 680009857-(5-Bromopyridin-2-yl)-7-azaspiro[3.5]nonan-2-ol

Product 1

HCID 687595777-[5-(4-Fluorophenyl)pyridin-2-yl]-7-azaspiro[3.5]nonan-2-olYield 70.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The process is performed according to the procedure described in Example 2 (step 2.7.). Starting with 0.138 g (0.46 mmol) of 7-(5-bromopyridin-2-yl)-7-azaspiro[3.5]nonan-2-ol, obtained in step 10.1., 0.078 g (0.56 mmol) of 4-fluorophenylboronic acid, 0.454 g (1.39 mmol) of caesium carbonate suspended in 3 mL of a 9/1 mixture of tetrahydrofuran and water. 0.038 g (0.05 mmol) of PdCl2dppf.CH2Cl2 is then added. 0.101 g of pure product is thus obtained in the form of a grey powder.

Workup

  1. customobtained in step 10.1

Sources & evidence

ORD record
ord-d9922b554e354ad98c5a3c022b3edadb
Source dataset
uspto-grants-2014_11
Patent number
US08889702B2

Reaction notes

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