N-Iodosuccinimide → HCID 67494530, compound

HRID 2047139Notes

Reaction equation

HRID 2047139 reaction equation
[CH3:1][Si:2]([CH3:42])([CH3:41])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[C:8]1[N:13]2[N:14]=[CH:15][CH:16]=[C:12]2[N:11]=[C:10]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[CH2:19][CH2:18]2)[CH:9]=1.C1C(=O)N([I:50])C(=O)C1>C(#N)C>[CH3:1][Si:2]([CH3:42])([CH3:41])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([I:50])=[C:12]2[N:11]=[C:10]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[O:24])[CH2:19][CH2:18]2)[CH:9]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 66733663HCID 66733663, compound

Product 1

HCID 67494530HCID 67494530, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of benzyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)piperidine-1-carboxylate (2.27 g, 3.7 mmol) in acetonitrile (15 mL) was added NIS (833 mg, 1 eq). After stirring 1.5 hour, solvent was removed and the residue was purified on silica gel. Elution with EtOAc/Hexanes (0-50%) gave the title compound (2.38 g, 86%) as gum.

Workup

  1. customsolvent was removed
  2. customthe residue was purified on silica gel
  3. washElution with EtOAc/Hexanes (0-50%)

Sources & evidence

ORD record
ord-303ceeb7fad140b387cab004a9f42ebf
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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