Zinc → HCID 178478122, compound

HRID 1295472Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][Br:6].[Zn:11]>>[Br-:6].[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][Zn+:11]

Participants

Reactant 2

HCID 23994Zinc

HCID 6397264-(Bromomethyl)-1,2-dichlorobenzene

Product 1

HCID 178478122HCID 178478122, compound

Procedure

A mixture of 3,4-dichlorobenzyl bromide (0.47 g, 1.96 mmol) and Rieke Zinc (3.0 ml, 5 g/100 ml THF, 2.35 mmol) was stirred overnight at r.t. in a flame-dried Schlenk tube and decanted to provide a 0.65M stock solution of 3,4-dichlorobenzyl zinc bromide. A solution of 8-bromo-9-butyl-9H-purin-6-ylamine (42.7 mg, 0.158 mol), Pd(dppf)Cl2 (16.8 mg, 0.020 mmol), and 3,4-dichlorobenzyl zinc bromide (0.61 ml, 0.65M in THF) was stirred in a flame-dried Schlenk tube at 66° C. overnight, quenched with sat. aq. NH4Cl and sat. aq. EDTA., extracted into EtOAc, dried and concentrated. Preparative TLC purification (EtOAc/CH2Cl2/MeOH 14:14:2) provided the title compound as a colorless oil (approx. 15 mg, 20%).

Workup

customdecanted

Sources & evidence

ORD record: ord-d2b3cb4447714472986ebe7660ee147b
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07241890B2

Reaction notes

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