N-Iodosuccinimide → 4-Benzyloxy-1-cyclopropylmethyl-3-iodo-1H-pyridin-2-one

HRID 516622Notes

Reaction equation

HRID 516622 reaction equation
[I:1]N1C(=O)CCC1=O.[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][N:20]([CH2:23][CH:24]2[CH2:26][CH2:25]2)[C:19](=[O:27])[CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)(=O)C>[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][N:20]([CH2:23][CH:24]2[CH2:25][CH2:26]2)[C:19](=[O:27])[C:18]=1[I:1])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 594970994-(Benzyloxy)-1-(cyclopropylmethyl)pyridin-2(1H)-one

Product 1

HCID 594971024-Benzyloxy-1-cyclopropylmethyl-3-iodo-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-Iodosuccinimide (2.64 g, 11.74 mmol) was added to a solution of intermediate D1 (3.0 g, 11.74 mmol) in acetic acid (40 ml). The reaction mixture was stirred at room temperature for 1 hour, after which it was concentrated in vacuo, purified by flash chromatography (silica gel; 0-3% methanol/DCM as eluent) and finally recrystallized from diethyl ether to afford intermediate D10 (4.12 g, 92%) as a solid.

Workup

  1. concentrationafter which it was concentrated in vacuo
  2. custompurified by flash chromatography (silica gel; 0-3% methanol/DCM as eluent)
  3. customfinally recrystallized from diethyl ether
  4. customto afford intermediate D10 (4.12 g, 92%) as a solid

Sources & evidence

ORD record
ord-2d9c4798af97422ba2e179cdbcb1bcd8
Source dataset
uspto-grants-2015_08
Patent number
US09114138B2

Reaction notes

Loading…