Methyl iodide → HCID 89995659, compound

HRID 523057Notes

Reaction equation

HRID 523057 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:5]=[CH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([C:14]1[CH:15]=[N:16][N:17]([CH2:19][C:20]([CH3:23])([OH:22])[CH3:21])[CH:18]=1)=[CH:9][CH:8]=2.I[CH3:25]>C1COCC1.CCOC(C)=O>[Cl:3][C:4]1[N:5]=[CH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([C:14]1[CH:15]=[N:16][N:17]([CH2:19][C:20]([O:22][CH3:25])([CH3:23])[CH3:21])[CH:18]=1)=[CH:9][CH:8]=2

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 89995738HCID 89995738, compound

Product 1

HCID 89995659HCID 89995659, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

NaH (60%, 18 mg) was added to a solution of 1-(4-(3-chloroisoquinolin-6-yl)-1H-pyrazol-1-yl)-2-methylpropan-2-ol (Preparation 22, 96 mg, 0.318 mmol) in THF (6 mL). After stirring for 15 minutes, iodomethane (0.1 mL, 0.57 mmol) was added. The resulting solution was stirred at 60° C. under microwave irradiation for 60 minutes. The reaction mixture was diluted with EtOAc, filtered and purified using Biotage silica gel column chromatography eluting with 25% EtOAc/cyclohexane to give the title compound as yellow oil (57 mg, 57%).

Workup

  1. stirringThe resulting solution was stirred at 60° C. under microwave irradiation for 60 minutes
  2. filtrationfiltered
  3. custompurified
  4. washeluting with 25% EtOAc/cyclohexane

Sources & evidence

ORD record
ord-3e236debb6e144c4ad892e1d314db285
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

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