Methyl iodide → HCID 86700291, compound

HRID 712505Notes

Reaction equation

HRID 712505 reaction equation
[CH3:1][C:2]1[C:6]2[CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10][C:5]=2[NH:4][N:3]=1.[C:18]([O-])([O-])=O.[K+].[K+].IC>CC(C)=O>[C:14]([O:13][C:11]([N:8]1[CH2:9][CH2:10][C:5]2[N:4]([CH3:18])[N:3]=[C:2]([CH3:1])[C:6]=2[CH2:7]1)=[O:12])([CH3:17])([CH3:16])[CH3:15].[CH3:18][N:3]1[C:2]([CH3:1])=[C:6]2[CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10][C:5]2=[N:4]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178434176HCID 178434176, compound

Product 2

HCID 86700291HCID 86700291, compoundYield 44.3%HCID 86729507HCID 86729507, compoundYield 37.97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of tert-butyl 3-methyl-6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate (7.50 g, 29.84 mmol, 1.0 eq) in acetone was added K2CO3 (13.00 g, 3.0 eq) and iodomethane (2.20 mL, 1.2 eq). The reaction mixture was heated to reflux for 1.5 h and concentrated in vacuo. The residue was chromatographed with a silica gel column (eluting agent: 90:1 (v/v) DCM/MeOH) to give the title compounds tert-butyl1,3-dimethyl-6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate (3.0 g, 37.97%) and tert-butyl 2,3-dimethyl-6,7-dihydro-2H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate (3.5 g, 44.30%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 252.32 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1.5 h
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed with a silica gel column (eluting agent: 90:1 (v/v) DCM/MeOH)

Sources & evidence

ORD record
ord-60ca9a207a1647d892711520daa0ba09
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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