N-Iodosuccinimide → 2-Butoxy-3-iodo-6-methylpyridin-4-amine

HRID 2192998Notes

Reaction equation

HRID 2192998 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([NH2:12])[CH:9]=[C:8]([CH3:13])[N:7]=1)[CH2:2][CH2:3][CH3:4].[I:14]N1C(=O)CCC1=O>C1COCC1>[CH2:1]([O:5][C:6]1[C:11]([I:14])=[C:10]([NH2:12])[CH:9]=[C:8]([CH3:13])[N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 593754742-Butoxy-6-methylpyridin-4-amine

Product 1

HCID 593754672-Butoxy-3-iodo-6-methylpyridin-4-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-butoxy-6-methylpyridin-4-amine (31 g, 0.17 mol) was dissolved in THF (500 mL), and then N-iodosuccinimide (32 g, 0.14 mol) was added portionwise at −78° C. The reaction mixture was stirred at the same temperature for 2 min. The reaction was quenched by addition of water, and the resulting mixture was extracted with ethyl acetate (2×600 mL). The combined organic layers were washed with brine (500 mL), dried over sodium sulfate, and concentrated. The crude was purified by silica gel column chromatography (petroleum ether) to afford 2-butoxy-3-iodo-6-methylpyridin-4-amine. 1H NMR (400 MHz, CDCl3): δ 6.10 (s, 1H), 4.49 (m, 2H), 4.29 (t, J=6.4 Hz, 2H), 2.284 (s, 1H), 1.75 (m, 2H), 1.50 (m, 2H), 0.98 (t, J=7.6 Hz, 3H). LRMS calc'd for (C10H151N2O) [M+H]+, 307; found 307.

Workup

  1. customThe reaction was quenched by addition of water
  2. extractionthe resulting mixture was extracted with ethyl acetate (2×600 mL)
  3. washThe combined organic layers were washed with brine (500 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude was purified by silica gel column chromatography (petroleum ether)

Sources & evidence

ORD record
ord-ebf9111f003b4af5a739664f6af4ba42
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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