Dichloromethane → Pivaloyl chloride

HRID 1454841Notes

Reaction equation

HRID 1454841 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][C:7]=1[CH3:8].C(N(CC)CC)C.C(Cl)[Cl:24]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:9])=[N:6][C:7]=1[CH3:8].[CH3:12][C:11]([CH3:14])([CH3:13])[C:10]([Cl:24])=[O:15]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 960161N-(5-bromo-6-methyl-pyridin-2-yl)-2,2-dimethyl-propionamide

Product 2

HCID 62493Pivaloyl chlorideHCID 1706782-Pyridinamine, 5-bromo-6-methyl-

Procedure

This material was prepared in analogy to example 107 step A] from N-(5-bromo-6-methyl-pyridin-2-yl)-2,2-dimethyl-propionamide, 7.05 g—obtained via standard acylation of 5-bromo-6-methyl-pyridin-2-ylamine with 2,2-dimethyl-propionyl chloride in CH2Cl2, with triethylamine as base, as viscous brown oil, MS (ESI): 271.2 (MH+)- butyllithium (34.94 mL, 1.6 M in hexane, Agros) and N,N-dimethylformamide (4 mL) as an amorphous light brown solid (5.7 g). MS (EI): 220.1 (M+)

Sources & evidence

ORD record
ord-9e3036ef1df1419cb73606988cb1c783
Source dataset
uspto-grants-2009_01
Patent number
US07482341B2

Reaction notes

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