1,1,3,3-Tetramethylbutyl isocyanide → (6-Iodo-imidazo[1,2-a]pyridin-3-yl)-(1,1,3,3-tetramethyl-butyl)-amine

HRID 751273Notes

Reaction equation

HRID 751273 reaction equation
[CH3:1][C:2]([N+:9]#[C-:10])([CH3:8])[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5].[I:11][C:12]1[CH:13]=[CH:14][C:15]([N:18]=[CH2:19])=[N:16][CH:17]=1>CO>[I:11][C:12]1[CH:13]=[CH:14][C:15]2[N:16]([C:10]([NH:9][C:2]([CH3:8])([CH3:1])[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[CH:19][N:18]=2)[CH:17]=1

Participants

4

Reactant 2

HCID 267251,1,3,3-Tetramethylbutyl isocyanideHCID 58611975(5-Iodopyridin-2-yl)-methylene-amine

Product 1

HCID 58611973(6-Iodo-imidazo[1,2-a]pyridin-3-yl)-(1,1,3,3-tetramethyl-butyl)-amineYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add 1,1,3,3-tetramethylbutyl isocyanide (Aldrich; 0.57 g, 4.06 mmol) to a solution of (5-iodo-pyridin-2-yl)-methylene-amine (Preparation 15a; 0.8 g, 3.4 mmol) in methanol (20 mL). Reflux for 36 h and concentrate. Purify by flash chromatography eluting with a gradient of 100% hexanes to 50% EtOAc/50% hexanes (45 mL/min, 44 min) giving 0.5 g (40%) of the title compound as a dark brown semi-solid. ES+ m/e 371.8 (M+1).

Workup

  1. temperatureReflux for 36 h
  2. concentrationconcentrate
  3. customPurify by flash chromatography
  4. washeluting with a gradient of 100% hexanes to 50% EtOAc/50% hexanes (45 mL/min, 44 min)

Sources & evidence

ORD record
ord-81919e261d184dc3961c28e866cd223c
Source dataset
uspto-grants-2008_07
Patent number
US07405299B2

Reaction notes

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