Hydrochloric Acid → HCID 67469068, compound

HRID 1850239Notes

Reaction equation

HRID 1850239 reaction equation
[Br:1][C:2]1[C:3]([CH:8]2[CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[ClH:19]>CO>[ClH:19].[NH:10]1[CH2:9][CH:8]([C:3]2[C:2]([Br:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[CH2:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58546913HCID 58546913, compound

Product 1

HCID 67469068HCID 67469068, compoundYield 108.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 3-(3-bromopyridin-2-yl)azetidine-1-carboxylate (3) (266 g, 0.849 mol, 1 eq.) in methanol (6 L) was added concentrated HCl (350 mL, 4.2 mol, 4.95 eq.) and the resulting mixture was stirred at RT for 92 hrs. The mixture was concentrated and dried using a rotavapor to obtain 230 g of 2-(azetidin-3-yl)-3-bromopyridine hydrochloride (4).

Workup

  1. concentrationThe mixture was concentrated
  2. customdried

Sources & evidence

ORD record
ord-e5017e7ff5b94ccf90111d6ad71d8222
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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