N-Iodosuccinimide → 7-(2-Chloro-5-fluoro-phenoxy)-4-hydroxy-1-iodo-isoquinoline-3-carboxylic acid ethyl ester

HRID 1480992Notes

Reaction equation

HRID 1480992 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[Cl:25])[CH:10]=2)=[O:5])[CH3:2].C1C(=O)N([I:33])C(=O)C1>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([I:33])[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[Cl:25])[CH:10]=2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 898130167-(2-Chloro-5-fluoro-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester

Product 1

HCID 898129217-(2-Chloro-5-fluoro-phenoxy)-4-hydroxy-1-iodo-isoquinoline-3-carboxylic acid ethyl esterYield 29.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 7-(2-chloro-5-fluoro-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester (459 mg) and NIS (343 mg) in DCM (13 mL) was refluxed overnight; then concentrated, the residue was column purified to give the desired product (184 mg). LC MS ESI: 488 (M+1)+.

Workup

  1. temperaturewas refluxed overnight
  2. concentrationthen concentrated
  3. custompurified

Sources & evidence

ORD record
ord-d3ff186eb2a4424785d7d2236283076c
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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