HCID 86673025, compound → HCID 136352219, compound

HRID 1853253Notes

Reaction equation

HRID 1853253 reaction equation
C([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][C:13]([Br:18])=[C:14]([CH3:17])[CH:15]=2)[O:10][C:9]([C:19]2[N:20]=[CH:21][C:22]3[C:27]([CH:28]=2)=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:8]1)(C)(C)C>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[Br:18][C:13]1[CH:12]=[C:11]2[C:16]([C:7](=[N:6][OH:5])[CH:8]=[C:9]([C:19]3[N:20]=[CH:21][C:22]4[C:27]([CH:28]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)[O:10]2)=[CH:15][C:14]=1[CH3:17]

Participants

4

Reactant 1

HCID 86673025HCID 86673025, compound

Product 1

HCID 136352219HCID 136352219, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

7-bromo-2-isoquinolin-3-yl-6-methyl-chromen-4-one oxime was prepared using the method D, (step 2) illustrated in example 1C. 7-bromo-2-isoquinolin-3-yl-6-methyl-chromen-4-one O-tert-butyl oxime (100 mg, 0.22 mmol) was treated with a 1M solution of titanium tetrachloride (0.68 ml, 0.68 mmol) in dichloromethane (4 ml) to yield 7-bromo-2-isoquinolin-3-yl-6-methyl-chromen-4-one oxime (79 mg, 94%) as a yellow solid after recrystallization in hot chloroform. The compound was isolated as a 88/12 mixture of Z/E oxime isomers.

Workup

  1. custom7-bromo-2-isoquinolin-3-yl-6-methyl-chromen-4-one oxime was prepared

Sources & evidence

ORD record
ord-f5dd95379063444f8827f879cf5134cd
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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