Isopropyl iodide → HCID 67517948, compound

HRID 589991Notes

Reaction equation

HRID 589991 reaction equation
[CH3:1][S:2][C:3]1[S:4][C:5]([C:13]2[CH:17]=[CH:16][N:15]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[N:14]=2)=[C:6]2[CH2:11][CH2:10][NH:9][C:8](=[O:12])[C:7]=12.[H-].[Na+].I[CH:29]([CH3:31])[CH3:30]>CN(C=O)C>[CH3:1][S:2][C:3]1[S:4][C:5]([C:13]2[CH:17]=[CH:16][N:15]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:24])([CH3:23])[CH3:25])[N:14]=2)=[C:6]2[CH2:11][CH2:10][N:9]([CH:29]([CH3:31])[CH3:30])[C:8](=[O:12])[C:7]=12

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 86701090HCID 86701090, compound

Product 1

HCID 67517948HCID 67517948, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(methylsulfanyl)-1-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazol-3-yl)-6,7-dihydrothieno[3,4-c]pyridin-4(5H)-one (30 mg, 0.076 mmol) in DMF (0.7 mL) at 0° C. was added NaH (1.8 mg, 0.076 mmol). After 10 min, 2-iodopropane (13 mg, 0.076 mmol) was added and the reaction mixture was stirred at rt overnight, The resulting mixture was concentrated and purified directly by silica gel chromatography (gradient elution, 0-40% EtOAc/hexanes) to afford the title compound. LRMS (ESI) m/z 438.0 [(M+H)+; calcd for C20H31N3O2S2Si: 438].

Workup

  1. concentrationThe resulting mixture was concentrated
  2. custompurified directly by silica gel chromatography (gradient elution, 0-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ac5852f480ab434e9c60ac166c88d6aa
Source dataset
uspto-grants-2016_01
Patent number
US09233977B2

Reaction notes

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