Benzyl Bromide → HCID 8166485, compound

HRID 1169873Notes

Reaction equation

HRID 1169873 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:6]([CH:9]=1)[CH2:7][NH2:8].ClC1C=CC([O:27]CC(N)=O)=C(C=1)CN.ClC1C=CC(O)=C(C=1)C(N)=O.C(Br)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>[Cu]I.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:6]([CH:9]=1)[C:7]([NH2:8])=[O:27]

Participants

8

Reactant 5

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 3480945-Chloro-2-hydroxybenzamide2×HCID 111834945-chloro-2-(aminocarbonylmethyloxy)benzylamineHCID 11436574HCID 11436574, compound

Product 1

HCID 8166485HCID 8166485, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

Compounds 72 and 73 were synthesized through a Sonogashira-type reaction in high yield using CuI and (Ph3P)PdCl2 as catalysts. Sonogashira et al., Tet. Lett. 1975, 4467-4470. For the preparation of both 5-chloro-2-benzyloxybenzylamine 76 and 5-chloro-2-(aminocarbonylmethyloxy)benzylamine 80, 5-chloro-2-hydroxybenzamide 74 was used as starting material. Compound 74 was treated with benzyl bromide in the presence of K2CO3 in N,N-dimethylformamide to obtain 5-chloro-2-benzyloxybenzamide 75 in 98% yield. Finally, the amide 75 was reduced to the corresponding amine 76 with LiAlH4 in tetrahydrofuran.

Workup

  1. customin high yield

Sources & evidence

ORD record
ord-2c873a37e9b54f529841cddf5b82f040
Source dataset
uspto-grants-2010_11
Patent number
US07825126B2

Reaction notes

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