HCID 66745967, compound → HCID 66745861, compound

HRID 1467002Notes

Reaction equation

HRID 1467002 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]#[C:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:3]=1[C:4]#[N:5]>CCOC(C)=O.CCO.[Pd]>[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:3]=1[C:4]#[N:5]

Participants

4

Reactant 1

HCID 66745967HCID 66745967, compound

Product 1

HCID 66745861HCID 66745861, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A suspension of 2-amino-6-(3,3-dimethylbut-1-ynyl)benzonitrile (Example 21c, 690 mg, 3.48 mmol) and 10% Pd/C (100 mg) in EtOAc/EtOH (1:1, 20 mL) was stirred under an atmosphere of H2 with a balloon at room temperature overnight. The Pd/C was removed by filtration, the filtrate was concentrated, and purified by chromatography on silica gel eluting with 20% EtOAc in hexanes to give the title compound as a light yellow oil (620 mg, 88%). 1H NMR (400 MHz, DMSO-d6) δ 0.92 (s, 9H), 1.36-1.40 (m, 2H), 2.52-2.56 (m, 2H), 5.88 (s, 2H), 6.45 (d, J=7.6 Hz, 1H), 6.57 (d, J=7.6 Hz, 1H), 7.15 (t, J=8.0 Hz, 1H). MS 203 (MH+).

Workup

  1. customThe Pd/C was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. custompurified by chromatography on silica gel eluting with 20% EtOAc in hexanes

Sources & evidence

ORD record
ord-eba5cdcd0b2c4c898f38b2291c4241e5
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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