Potassium Carbonate → HCID 67517961, compound

HRID 589993Notes

Reaction equation

HRID 589993 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.I[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[Cu]I>[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]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:8](=[O:12])[C:7]=12

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 86701090HCID 86701090, compound

Product 1

HCID 67517961HCID 67517961, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

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 (Example 3) (20 mg, 0.051 mmol) in DMF (120 μL) at rt was added iodobenzene (21 mg, 0.101 mmol), K2CO3 (7 mg, 0.051 mmol) and CuI (1.0 mg, 0.0051 mmol). The reaction mixture was heated at 150° C. for 72 h. The resulting mixture was concentrated and purified directly by silica gel chromatography (gradient elution, 0-50% EtOAc/hexanes) to afford the title compound. LRMS (ESI) m/z 471.9 [(M+H)+; calcd for C23H29N3O2S2Si: 472].

Workup

  1. concentrationThe resulting mixture was concentrated
  2. custompurified directly by silica gel chromatography (gradient elution, 0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-77ced350d573443d885379aaf959ce16
Source dataset
uspto-grants-2016_01
Patent number
US09233977B2

Reaction notes

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