5-Bromo-2-fluoropyridine → HCID 68000491, compound

HRID 336550Notes

Reaction equation

HRID 336550 reaction equation
FC(F)(F)C(O)=O.[CH2:8]1[C:11]2([CH2:15][CH2:14][NH:13][CH2:12]2)[CH2:10][CH:9]1[NH:16][C:17]([O:19][CH2:20][C:21]1[O:25][N:24]=[C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:22]=1)=[O:18].F[C:32]1[CH:37]=[CH:36][C:35]([Br:38])=[CH:34][N:33]=1>ClCCl.CO>[Br:38][C:35]1[CH:36]=[CH:37][C:32]([N:13]2[CH2:14][CH2:15][C:11]3([CH2:10][CH:9]([NH:16][C:17]([O:19][CH2:20][C:21]4[O:25][N:24]=[C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:22]=4)=[O:18])[CH2:8]3)[CH2:12]2)=[N:33][CH:34]=1

Participants

5

Reactant 2

HCID 27831685-Bromo-2-fluoropyridineHCID 68001495HCID 68001495, compound

Product 1

HCID 68000491HCID 68000491, compoundYield 137.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

The process is performed according to the procedure described in Example 2 (step 2.6.). Starting with 0.43 g (1.03 mmol) of ethyl 5-(6-azaspiro[3.4]oct-2-ylcarbamoyloxymethyl)isoxazole-3-carboxylate trifluoroacetate (isomer 5′), obtained in step 12.5., and 0.45 g (2.60 mmol) of 2-fluoro-5-bromopyridine, and after chromatography on silica gel, eluting with a 97/3 mixture of dichloromethane and methanol, 0.68 g of pure product is obtained in the form of an oil.

Workup

  1. customobtained in step 12.5

Sources & evidence

ORD record
ord-6bc5c8b482014af59decb2969aef40f1
Source dataset
uspto-grants-2014_11
Patent number
US08889702B2

Reaction notes

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