Diisopropylethylamine → 4-(5'-Bromo-3'-fluoro-2,3,5,6-tetrahydro-[1,2']bipyridinyl-4-ylideneaminooxy)-piperidine-1-carboxylic acid isopropyl ester

HRID 2066857Notes

Reaction equation

HRID 2066857 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4](=[N:7][O:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH2:3][CH2:2]1.[Br:21][C:22]1[CH:23]=[N:24][C:25](Cl)=[C:26]([F:28])[CH:27]=1.C(N(C(C)C)CC)(C)C>CS(C)=O>[CH:18]([O:17][C:15]([N:12]1[CH2:11][CH2:10][CH:9]([O:8][N:7]=[C:4]2[CH2:3][CH2:2][N:1]([C:25]3[C:26]([F:28])=[CH:27][C:22]([Br:21])=[CH:23][N:24]=3)[CH2:6][CH2:5]2)[CH2:14][CH2:13]1)=[O:16])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27632855-Bromo-2-chloro-3-fluoropyridineHCID 57461147Isopropyl 4-(Piperidin-4-ylideneaminooxy)piperidine-1-carboxylate

Product 1

HCID 866550094-(5'-Bromo-3'-fluoro-2,3,5,6-tetrahydro-[1,2']bipyridinyl-4-ylideneaminooxy)-piperidine-1-carboxylic acid isopropyl esterYield 28.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2d (0.22 g, 0.71 mmol), 3-bromo-6-chloro-5-fluoro-pyridine (0.2 g, 0.95 mmol) and diisopropylethylamine (0.2 mL, 1.2 mmol) in 2 mL of DMSO were heated at 130° C. for 20 h. The mixture was cooled to room temperature and purified by flash LC(0 to 30% EtOAc+0.1% triethylamine in hexane) to afford 46a (92 mg, 28% yield): HPLC, LC-MS 457.1 (MH).

Workup

  1. custompurified by flash LC(0 to 30% EtOAc+0.1% triethylamine in hexane)

Sources & evidence

ORD record
ord-65461793d462409bbd3185334507dcd5
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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