HCID 86673027, compound → HCID 136352220, compound

HRID 1853255Notes

Reaction equation

HRID 1853255 reaction equation
C([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Br:17])[CH:15]=2)[O:10][C:9]([C:18]2[N:19]=[CH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:8]1)(C)(C)C>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[Br:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[O:10][C:9]([C:18]1[N:19]=[CH:20][C:21]3[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:8][C:7]2=[N:6][OH:5]

Participants

4

Reactant 1

HCID 86673027HCID 86673027, compound

Product 1

HCID 136352220HCID 136352220, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

6-bromo-2-isoquinolin-3-yl-chromen-4-one oxime was prepared using the method D, (step 2) illustrated in example 1C. 6-bromo-2-isoquinolin-3-yl-chromen-4-one O-tert-butyl oxime (50 mg, 0.12 mmol) was treated with a 1M solution of titanium tetrachloride (0.35 ml, 0.35 mmol) in dichloromethane (3 ml) to yield 6-bromo-2-isoquinolin-3-yl-chromen-4-one oxime (37 mg, 85%) as a yellow solid after recrystallization in hot chloroform. The compound was isolated as a 98/2 mixture of Z/E oxime isomers.

Workup

  1. custom6-bromo-2-isoquinolin-3-yl-chromen-4-one oxime was prepared

Sources & evidence

ORD record
ord-e82509a5771b47c09fa600231aad616c
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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