Methanol → 2-(Azetidin-3-yloxy)-5-iodo-pyridine hydrochloride

HRID 1469354Notes

Reaction equation

HRID 1469354 reaction equation
[Cl:1]C(OC(Cl)C)=O.C([N:21]1[CH2:24][CH:23]([O:25][C:26]2[CH:31]=[CH:30][C:29]([I:32])=[CH:28][N:27]=2)[CH2:22]1)(C1C=CC=CC=1)C1C=CC=CC=1.CO>ClCCl>[ClH:1].[NH:21]1[CH2:22][CH:23]([O:25][C:26]2[CH:31]=[CH:30][C:29]([I:32])=[CH:28][N:27]=2)[CH2:24]1

Participants

5

Reactant 3

HCID 887MethanolHCID 5213051-Chloroethyl chloroformateHCID 580731012-(1-Benzhydryl-azetidin-3-yloxy)-5-iodo-pyridine

Product 1

HCID 667101622-(Azetidin-3-yloxy)-5-iodo-pyridine hydrochlorideYield 109.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-chloroethyl chloroformate (12.8 mL, 0.104 mol) was added drop-wise via syringe to a stirred solution of 2-(1-Benzhydryl-azetidin-3-yloxy)-5-iodo-pyridine (23.03 g, 0.052 mol) in dichloromethane (250 mL) at ambient temperature. The resulting solution was stirred at ambient temperature for 3.5 hr, then methanol (250 mL) was added and the reaction mixture stirred at ambient temperature for 16 hr. The solvents were then removed in vacuo and the resulting solid residue was triturated with diethyl ether, filtered and then dried in vacuo to afford the title product as a cream-coloured solid (17.8 g, >quant yield). The crude product was used directly without further purification.

Workup

  1. stirringthe reaction mixture stirred at ambient temperature for 16 hr
  2. customThe solvents were then removed in vacuo
  3. customthe resulting solid residue was triturated with diethyl ether
  4. filtrationfiltered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-3c1a2a05a5b547de87e387d3647f6197
Source dataset
uspto-grants-2015_04
Patent number
US09006269B2

Reaction notes

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