Triethylamine → HCID 57885856, compound

HRID 659368Notes

Reaction equation

HRID 659368 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([I:11])=[CH:4][N:3]=1.Cl.[NH2:13][C:14]([CH3:20])([CH3:19])[C:15]([O:17][CH3:18])=[O:16].C(N(CC)CC)C>C(O)C>[CH3:18][O:17][C:15](=[O:16])[C:14]([NH:13][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([I:11])=[CH:4][N:3]=1)([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15142942-Chloro-5-iodo-3-nitropyridineHCID 13258034Methyl 2-aminoisobutyrate hydrochloride

Product 1

HCID 57885856HCID 57885856, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

2-Chloro-5-iodo-3-nitro-pyridine (1.61 g) was dissolved in ethanol. Methyl α-aminoisobutyrate HCl was added (2.4 eq) followed by triethylamine (2.4 eq). The reaction mixture was heated to 150° C. in a microwave oven for 30 minutes. The reaction mixture was concentrated to dryness and triturated with H2O, Silica gel chromatography of the resulting brown solid afforded the title compound as a bright yellow crystalline solid (78% yield based on recovered starting material). M.p. 121-122° C., 1H-NMR (CDCl3, 400 MHz) δ 1.56 (s, 3H), 1.66 (s, 3H), 3.67 (s, 3H), 8.53 (s, 1H), 8.47 (d, J=2.0 Hz, 1H), 8.68 (d, J=2.3 Hz, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customtriturated with H2O, Silica gel chromatography of the resulting brown solid

Sources & evidence

ORD record
ord-813040edf9d648ae9e298be69c74115b
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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