HCID 14802113, compound → HCID 66697275, compound

HRID 2386745Notes

Reaction equation

HRID 2386745 reaction equation
[CH3:1][N:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12]([OH:14])=O)[C:6]=2[O:5][CH2:4][C:3]1=[O:15].[Br:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23]Br)=[C:19]([Cl:25])[CH:18]=1>[Zn].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:12]([C:11]2[C:6]3[O:5][CH2:4][C:3](=[O:15])[N:2]([CH3:1])[C:7]=3[CH:8]=[CH:9][CH:10]=2)=[O:14])=[C:19]([Cl:25])[CH:18]=1

Participants

5

Reactant 2

HCID 14802113HCID 14802113, compoundHCID 219144864-Bromo-1-(bromomethyl)-2-chlorobenzene

Product 1

HCID 66697275HCID 66697275, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

In analogy to Example 49, step 1, 4-methyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid (CAS Reg. No. 1017273-27-6) was converted to the acid chloride and subsequently reacted with 4-bromo-1-bromomethyl-2-chloro-benzene in the presence of zinc and tetrakis(triphenylphosphine)palladium(0) to give the title compound as a colorless solid. MS (m/e, ISP neg. ion)=392.1 [M−H+].

Sources & evidence

ORD record
ord-07225f27431843eab1dbaa8bef8fa9e2
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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