HCID 74020022, compound → HCID 23132385, compound

HRID 661720Notes

Reaction equation

HRID 661720 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][O:11][NH:12][C:13](=[O:37])[C:14]1[CH:19]=[C:18]([CH:20]=[N:21][O:22][CH2:23][CH:24]=[O:25])[C:17]([F:26])=[C:16]([F:27])[C:15]=1[NH:28][C:29]1[CH:34]=[CH:33][C:32]([I:35])=[CH:31][C:30]=1[F:36])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:38][Mg]Br>O1CCCC1>[Si:1]([O:8][CH2:9][CH2:10][O:11][NH:12][C:13](=[O:37])[C:14]1[CH:19]=[C:18](/[CH:20]=[N:21]/[O:22][CH2:23][CH:24]([OH:25])[CH3:38])[C:17]([F:26])=[C:16]([F:27])[C:15]=1[NH:28][C:29]1[CH:34]=[CH:33][C:32]([I:35])=[CH:31][C:30]=1[F:36])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 74020022HCID 74020022, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 23132385HCID 23132385, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

N-[2-(t-butyldimethylsilanyloxy)-ethoxy]-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-5-[(2-oxo-ethoxyimino)-methyl]-benzamide (60 mg, 0.092 mmol) prepared in Process A was dissolved in anhydrous tetrahydrofuran (2.0 mL) under an argon atmosphere. This reaction solution was cooled to −78° C., and then 0.93 M methyl magnesium bromide (0.25 mL) was added thereto. The reaction solution was allowed to gradually warm to room temperature, and stirred for eight hours. The reaction was quenched with saturated aqueous solution of ammonium chloride, and the solution was extracted with ethyl acetate.

Workup

  1. temperatureto gradually warm to room temperature
  2. customThe reaction was quenched with saturated aqueous solution of ammonium chloride
  3. extractionthe solution was extracted with ethyl acetate

Sources & evidence

ORD record
ord-ee8e895d31324de3bb139d9fee4e1242
Source dataset
uspto-grants-2011_12
Patent number
US08084645B2

Reaction notes

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