Dichloromethane → (2S)-2-[5-(4-chloro-1-methyl-1H-pyrazol-5-yl)-1-oxo-1,3-dihydro-2H-isoindol-2-yl]-3-(3-fluorophenyl)propanal

HRID 339968Notes

Reaction equation

HRID 339968 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH3:28])[C:6]=1[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[N:11]([C@@H:17]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=1)[CH2:18][OH:19])[CH2:10]2.C(Cl)Cl.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>>[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH3:28])[C:6]=1[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[N:11]([C@@H:17]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=1)[CH:18]=[O:19])[CH2:10]2

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 866814605-(4-chloro-1-methyl-1H-pyrazol-5-yl)-2-[(1S)-1-(3-fluorobenzyl)-2-hydroxyethyl]isoindolin-1-one

Product 1

HCID 86681462(2S)-2-[5-(4-chloro-1-methyl-1H-pyrazol-5-yl)-1-oxo-1,3-dihydro-2H-isoindol-2-yl]-3-(3-fluorophenyl)propanalYield 86%

Procedure

To a solution of 5-(4-chloro-1-methyl-1H-pyrazol-5-yl)-2-[(1S)-1-(3-fluorobenzyl)-2-hydroxyethyl]isoindolin-1-one (0.8 g, 2.001 mmol) in methylene chloride (10 mL, 200 mmol) at 0° C. was added Dess-Martin periodinane (1.02 g, 2.40 mmol). The reaction mixture was stirred at room temperature for 1 h, and then quenched with 1 N NaOH aqueous solution, and extracted with DCM (2×). The combined organic phases were washed with water, brine and dried over Na2SO4, filtered and concentrated under reduced pressure to give 685 mg (86% yield) of the desired product as yellowish solid. LC/MS found: 398.1 (M+H)+.

Workup

  1. customquenched with 1 N NaOH aqueous solution
  2. extractionextracted with DCM (2×)
  3. washThe combined organic phases were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7caac3b84f7647619e6f343bf8b7f68a
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

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