4-Bromo-1-(bromomethyl)-2-chlorobenzene → HCID 67546105, compound

HRID 2386741Notes

Reaction equation

HRID 2386741 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH2:6][O:5][C:4]2[N:9]=[CH:10][C:11]([C:13]([OH:15])=O)=[CH:12][C:3]1=2.[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:13]([C:11]2[CH:10]=[N:9][C:4]3[O:5][CH2:6][C:7](=[O:8])[N:2]([CH3:1])[C:3]=3[CH:12]=2)=[O:15])=[C:19]([Cl:25])[CH:18]=1

Participants

5

Reactant 2

HCID 219144864-Bromo-1-(bromomethyl)-2-chlorobenzeneHCID 675461162,3-Dihydro-1-methyl-2-oxo-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylic acid

Product 1

HCID 67546105HCID 67546105, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

In analogy to Example 49, step 1, 1-methyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylic acid 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 light yellow solid. MS (m/e, ISP neg. ion)=392.9 [M−H+].

Sources & evidence

ORD record
ord-e1fb17807dc540c19e72b9f8b9c2b9c7
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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