Methanol → 3-[(E)-2-(4-fluorophenyl)ethenyl]-N-[1-(2-hydroxyethyl)cyclopropyl]-4-methoxy-1H-indazole-5-carboxamide

HRID 34107Notes

Reaction equation

HRID 34107 reaction equation
C(O[CH:9]([C:11]1([NH:14][C:15]([C:17]2[C:18]([O:35][CH3:36])=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][N:21]=[C:20]3/[CH:26]=[CH:27]/[C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[O:16])[CH2:13][CH2:12]1)C)C1C=CC=CC=1.C[Si](I)(C)C.[CH3:42][OH:43]>ClCCl>[OH:43][CH2:42][CH2:9][C:11]1([NH:14][C:15]([C:17]2[C:18]([O:35][CH3:36])=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][N:21]=[C:20]3/[CH:26]=[CH:27]/[C:28]2[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=2)=[O:16])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 86600699HCID 86600699, compound

Product 1

HCID 600348833-[(E)-2-(4-fluorophenyl)ethenyl]-N-[1-(2-hydroxyethyl)cyclopropyl]-4-methoxy-1H-indazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

20 mg of 3-[(E)-2-(4-fluorophenyl)-vinyl]-4-methoxy-1H-indazole-5-carboxylic acid (1-benzyloxyethyl-cyclopropyl)-amide obtained by Example 814 was dissolved in 1 mL of dichloromethane, added with 6.4 μl of trimethylsilyliodide at 0° C. under nitrogen atmosphere, and stirred at this temperature for 2 hours. The reaction solution was added with methanol to stop the reaction, and the solvent was concentrated, followed by purification by LC-MS, to afford 1.7 mg of the title compound.

Workup

  1. customthe reaction
  2. concentrationthe solvent was concentrated
  3. customfollowed by purification by LC-MS

Sources & evidence

ORD record
ord-f07ad732874947a08d3fcb2c79667574
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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