Hydrochloric Acid → (1s,4s)-2-(5-Bromo-pyridin-2-yl)-6-methyl-2,6-diaza-bicyclo[2.2.1]heptane

HRID 1916584Notes

Reaction equation

HRID 1916584 reaction equation
Br.Br.[CH3:3][N:4]1[CH2:9][C@@H:8]2[CH2:10][C@H:5]1CN2.[CH2:11]([N:13](C(C)C)C(C)C)C.Br[C:21]1[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][N:22]=1.Cl.C([O-])([O-])=O.[K+].[K+]>C(O)CCC.CCOC(C)=O>[Br:27][C:24]1[CH:25]=[CH:26][C:21]([N:13]2[CH2:11][C@H:8]3[CH2:10][C@H:5]2[N:4]([CH3:3])[CH2:9]3)=[N:22][CH:23]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 693532,5-DibromopyridineHCID 81531DiisopropylethylamineHCID 15629279(1S)-2-methyl-2,5-diazobicyclo[2.2.1]heptane dihydrobromide

Product 1

HCID 69075398(1s,4s)-2-(5-Bromo-pyridin-2-yl)-6-methyl-2,6-diaza-bicyclo[2.2.1]heptane

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 300 mg (1.10 mmol) (1S,4S)-2-methyl-2,5-diazabicylo[2.2.1]heptane dihydrobromide, 0.75 mL (4.40 mmol) ethyldiisopropylamine and 270 mg (1.11 mmol) 2,5-dibromopyridine in 1.5 mL n-butanol are stirred for 18 h at 115° C. The solvent is eliminated i.vac., the residue is combined with 10 mL EtOAc and acidified with 1 M HCl. The aqueous phase is twice made alkaline with 2 M K2CO3 solution and extracted with 30 mL EtOAc. The combined organic extracts are dried over Na2SO4 and the solvent is eliminated i.vac.

Workup

  1. extractionextracted with 30 mL EtOAc
  2. dry with materialThe combined organic extracts are dried over Na2SO4

Sources & evidence

ORD record
ord-b2c38fd3c01f4f449416884ad2e28daa
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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