Zinc → HCID 178491864, compound

HRID 853761Notes

Reaction equation

HRID 853761 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH2:6][Cl:7].[Zn:15].NC1C=CC(I)=CC=1C#N>C1COCC1>[Cl-:7].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH2:6][Zn+:15]

Participants

5

Reactant 3

HCID 23994ZincHCID 774485-(Chloromethyl)-1,2,3-trimethoxybenzeneHCID 99648032-Amino-5-iodobenzonitrile

Product 1

HCID 178491864HCID 178491864, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,4,5-Trimethoxybenzylzinc chloride was prepared from 3,4,5-trimethoxybenzyl chloride (867 mg, 4 mmol) and reactive metallic zinc suspension (0.76 M in THF, 6.3 mL, 4.8 mmol). The supernatant was transferred via a cannula into a solution of 9 (244 g, 1 mmol) in THF, followed by the usual workup; pale-yellow oil (127 mg, 43%): 1H NMR (CDCl3) δ 3.78 (s, 2H, CH2), 3.81 (s, 6H, 3′- and 5′-OMe), 3.82 (s, 3H, 4′-OMe), 4.28 (br s, NH2), 6.30 (s, 2H, H-2′ and H-6′), 6.69 (d, J=8.4 Hz, 1H, H-3), 7.16 (d, J=8.4 Hz, 1H, H-4), 7.19 (s, 1H, H-6).

Sources & evidence

ORD record
ord-91a4d3c0772642e1a0a783bb6cb7df78
Source dataset
uspto-grants-2007_08
Patent number
US07256197B2

Reaction notes

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