Bromine → HCID 59132185, compound

HRID 1993103Notes

Reaction equation

HRID 1993103 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[Br:12]Br>C(Cl)(Cl)(Cl)Cl>[Br:12][C:9]1[CH:10]=[CH:11][C:2]([OH:1])=[C:3]2[C:8]=1[CH:7]=[N:6][CH:5]=[CH:4]2

Participants

4

Reactant 2

HCID 24408BromineHCID 30386Isoquinolin-5-ol

Product 1

HCID 59132185HCID 59132185, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

For example, 5-hydroxyisoquinoline 66.7 is reacted with bromine in carbon tetrachloride to afford 8-bromo-5-hydroxyisoquinoline 66.8. The product is reacted with acetic anhydride in pyridine to give 5-acetoxy-8-bromoisoquinoline 66.9. The latter compound is coupled with a dialkyl propenyl phosphonate 66.10 (Aldrich) in the presence of ca. 3 mol % of bis(triphenylphosphine)palladium(II) chloride and triethylamine, in dimethylformamide at ca. 60°, to produce the coupled product 66.11. The acetyl protecting group is then removed by reaction with dilute aqueous methanolic ammonia, as described in J. Chem. Soc., 2137, 1964, to afford the phenol 66.12. The product is optionally reduced to yield the saturated analog 66.13. The reduction reaction is effected chemically, for example by the use of diimide or diborane, as described in Comprehensive Organic Transformations, by R. C. Larock, VCH, 1989, p. 5, or catalytically.

Sources & evidence

ORD record
ord-2493b8a8e6df4bf085e9140037093f5f
Source dataset
uspto-grants-2010_01
Patent number
US07649015B2

Reaction notes

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