Trimethylsilyl iodide → 3,4-dichloro-N-[1-(5-cyano-4-hydroxy-1,3-thiazol-2-yl)piperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide

HRID 2234028Notes

Reaction equation

HRID 2234028 reaction equation
I[Si](C)(C)C.[Cl:6][C:7]1[C:11]([Cl:12])=[C:10]([CH3:13])[NH:9][C:8]=1[C:14]([NH:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]2[S:24][C:25]([C:30]#[N:31])=[C:26]([O:28]C)[N:27]=2)[CH2:19][CH2:18]1)=[O:15]>C(Cl)Cl.C(Cl)(Cl)Cl>[Cl:6][C:7]1[C:11]([Cl:12])=[C:10]([CH3:13])[NH:9][C:8]=1[C:14]([NH:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]2[S:24][C:25]([C:30]#[N:31])=[C:26]([OH:28])[N:27]=2)[CH2:19][CH2:18]1)=[O:15]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 685799323,4-dichloro-N-[1-(5-cyano-4-methoxy-1,3-thiazol-2-yl)piperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide

Product 1

HCID 685798543,4-dichloro-N-[1-(5-cyano-4-hydroxy-1,3-thiazol-2-yl)piperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 18399249Chloroform dichloromethaneSolvent

Procedure

Iodotrimethylsilane (0.02 ml, 0.13 mmol) was added to a suspension of 3,4-dichloro-N-[1-(5-cyano-4-methoxy-1,3-thiazol-2-yl)piperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide (Example 269, 0.04 g, 0.1 mmol) in DCM:CHCl3 (1:1). After stirring for one hour the reaction was complete. Partitioning with EtOAc and water, drying organic portion with MgSO4 and concentrating yielded a yellow oil which, after triturating with ether, gave a yellow solid.

Workup

  1. customPartitioning with EtOAc and water
  2. dry with materialdrying organic portion with MgSO4
  3. concentrationconcentrating
  4. customyielded a yellow oil which
  5. customafter triturating with ether
  6. customgave a yellow solid

Sources & evidence

ORD record
ord-91c830b5cec84db29fc804df2beb6f7a
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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