HCID 178418361, compound → HCID 178507171, compound

HRID 1805296Notes

Reaction equation

HRID 1805296 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]=[C:2]1[C:10]1([NH:13]C(=O)OCC2C=CC=CC=2)[CH2:12][CH2:11]1.[H][H]>CO.[Pd+2]>[NH:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]=[C:2]1[C:10]1([NH2:13])[CH2:11][CH2:12]1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178521694HCID 178521694, compound

Product 1

HCID 178507171HCID 178507171, compoundYield 120.5%

Reagents, catalysts & solvents 2

HCID 105144Allyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)chloropalladium(II)CatalystHCID 887MethanolSolvent

Procedure

To a small RBF was added benzyl 1-(1H-imidazo[4,5-c]pyridin-2-yl)cyclopropylcarbamate (939 mg, 3.05 mmol) in methanol (13 ml). The flask was sealed with a septa and the solution was degassed and flushed with nitrogen several times. To the solution was then added 10% Palladium(II) on carbon (97 mg, 91 μmol), and a balloon of hydrogen was added to the top of the flask. The mixture was stirred overnight at room temperature. The mixture was pushed through a plug of celite in a Whatman Autovial (equipped with a 0.45 uM nylon membrane and a glass microfiber prefilter). Volatiles were removed giving 640 mgs (100% yield) of 1-(1H-imidazo[4,5-c]pyridin-2-yl)cyclopropanamine as a yellow solid. 1H NMR (400 MHz, CD3OD) δ ppm 1.67-1.72 (m, 2 H), 1.73-1.80 (m, 2 H), 7.92 (m, 1 H), 8.40 (d, J=7.0 Hz, 1 H), 9.05 (s, 1 H). LCMS rt=0.293 min., m/z 175.1 (M+H), 90.7% purity.

Workup

  1. customThe flask was sealed with a septa
  2. customthe solution was degassed
  3. customflushed with nitrogen several times
  4. customVolatiles were removed

Sources & evidence

ORD record
ord-5d1d28116911488d815dc15616c1566b
Source dataset
uspto-grants-2013_01
Patent number
US08354410B2

Reaction notes

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