C16H22F6IN2P → Ethyl 7-bromo-4-hydroxy-1-iodo-3-isoquinolinecarboxylate
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]([Br:17])[CH:10]=2)=[O:5])[CH3:2].CC1C=C(C)N=C(C)C=1.CC1C([IH+:34])=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:7]=[C:8]([I:34])[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([Br:17])[CH:10]=2)=[O:5])[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
7-Bromo-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester (1.0 g, 3.37 mmol) was dissolved in dry dichloromethane (30 mL) and bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate (3.5 g, 6.754 mmol) was added in one portion as a solid. The solution was protected from light and permitted to stir overnight at room temperature. Upon completion, the reaction was quenched by addition of aqueous sodium thiosulfate (2.0 g in 50 mL of water. The layers were separated and the organic phase washed with 1M hydrochloric acid, brine and dried over anhydrous sodium sulfate. The crude material was purified by silica gel chromatography (3-15% ethyl acetate in hexanes) to provide the iodo-isoquinoline in 77% yield which was used immediately in the next step.
Workup
- customUpon completion, the reaction was quenched by addition of aqueous sodium thiosulfate (2.0 g in 50 mL of water
- customThe layers were separated
- washthe organic phase washed with 1M hydrochloric acid, brine
- dry with materialdried over anhydrous sodium sulfate
- customThe crude material was purified by silica gel chromatography (3-15% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-d705a3f60edf48d1b4ebb19b4a5af32d
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409892B2
Reaction notes
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