C16H22F6IN2P → 7-Hydroxy-4-iodo-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

HRID 642378Notes

Reaction equation

HRID 642378 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[S:14][C:8]=2[C:7]=1[OH:21])=[O:5])[CH3:2].CC1C=C(C)N=C(C)C=1.CC1C([IH+:38])=C(C)N=C(C)C=1.F[P-](F)(F)(F)(F)F>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([I:38])[C:9]2[N:12]=[C:13]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[S:14][C:8]=2[C:7]=1[OH:21])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 46863890C16H22F6IN2PHCID 684263587-Hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

Product 1

HCID 866173617-Hydroxy-4-iodo-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl esterYield 69.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (1.02 g, 3.39 mmole) and bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate (2.61 g, 5.08 mmole) in dichloromethane (30 ml) was stirred at room temperature for 16 h before it was concentrated and purified by flash column chromatography on silica gel with a gradient of dichloromethane and hexanes to give the title compound as a yellow solid (1.00 g). MS: (+) m/z 427.05 (M+1), MS: (−) m/z 425.01 (M−1).

Workup

  1. concentrationwas concentrated
  2. custompurified by flash column chromatography on silica gel with a gradient of dichloromethane and hexanes

Sources & evidence

ORD record
ord-2cbd8ef9a73b49adae1c83a161faed56
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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