Isobutylamine → HCID 63589320, compound

HRID 594105Notes

Reaction equation

HRID 594105 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[N:3]=1.[CH2:10]([NH2:14])[CH:11]([CH3:13])[CH3:12].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].O1CCCC1>>[CH3:9][O:8][C:4]1[N:3]=[C:2]([NH:14][CH2:10][CH:11]([CH3:13])[CH3:12])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 4

HCID 6558IsobutylamineHCID 8028TetrahydrofuranHCID 870092-Chloro-6-methoxypyridineHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 63589320HCID 63589320, compoundYield 7%

Conditions

Temperature
70 °C

Procedure

To a mixture of 2-chloro-6-methoxypyridine (357 μL, 3 mmol), isobutylamine (596 μL, 6.00 mmol) and Caddick's Catalyst (prepared according to the literature reference Org. Biomol. Chem. 2008, 6, 2820) (35.3 mg, 0.060 mmol) under nitrogen, was added lithium hexamethyldisilazide in tetrahydrofuran (THF) (1 M, 3.750 mL, 3.75 mmol). This was warmed to 70° C. and stirred overnight, then cooled for analysis. The reaction was then further heated by microwaves to 150° C. for 30 minutes. After cooling, purification was attempted by flash silica (Si) chromatography (0-50% dichloromethane-cyclohexane gradient), but this failed to provide adequate separation. Purification was then repeated by flash silica (Si) chromatography (0-65% dichloromethane-cyclohexane gradient) to isolate the title compound (37.8 mg). LCMS (2 min, formic) Rt 0.75 min, m/z (ES+) 181 (M+H).

Workup

  1. customprepared
  2. temperaturecooled for analysis
  3. temperatureThe reaction was then further heated by microwaves to 150° C. for 30 minutes
  4. temperatureAfter cooling
  5. custompurification
  6. customto provide adequate
  7. customseparation
  8. customPurification

Sources & evidence

ORD record
ord-26be4a653da6490c9a6ad6f593540d86
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

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