HCID 86673023, compound → HCID 136352218, compound

HRID 1853251Notes

Reaction equation

HRID 1853251 reaction equation
C([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][C:13]([Br:17])=[CH:14][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:13]1[CH:12]=[C:11]2[C:16]([C:7](=[N:6][OH:5])[CH:8]=[C:9]([C:18]3[N:19]=[CH:20][C:21]4[C:26]([CH:27]=3)=[CH:25][CH:24]=[CH:23][CH:22]=4)[O:10]2)=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 86673023HCID 86673023, compound

Product 1

HCID 136352218HCID 136352218, compoundYield 43.6%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

7-bromo-2-isoquinolin-3-yl-chromen-4-one oxime was prepared using the method D, (step 2) illustrated in example 1C. 7-bromo-2-isoquinolin-3-yl-chromen-4-one O-tert-butyl oxime (150 mg, 0.35 mmol) was treated with a 1M solution of titanium tetrachloride (1.1 ml, 1.1 mmol) in dichloromethane (7.5 ml) to yield 7-bromo-2-isoquinolin-3-yl-chromen-4-one oxime (56 mg, 37%) as a beige solid after recrystallization in hot chloroform. The product was isolated as a 90/10 mixture of Z/E oxime isomers.

Workup

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

Sources & evidence

ORD record
ord-b80ffd757d4c438995468b67d577cc26
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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