Sodium cyanoborohydride → 1h-Isoindole-5-carboxylic acid,2,3-dihydro-2-methyl-7-[4-(methylsulfonyl)phenoxy]-3-oxo-,methyl ester

HRID 1177363Notes

Reaction equation

HRID 1177363 reaction equation
[CH:1]([C:3]1[C:12]([O:13][C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[C:24]([O:26]C)=O)=O.Cl.NC.[BH3-][C:32]#[N:33].[Na+]>CO>[CH3:32][N:33]1[C:24](=[O:26])[C:4]2[C:3](=[C:12]([O:13][C:14]3[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=3)[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=2)[CH2:1]1

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 86624769HCID 86624769, compound

Product 1

HCID 667555411h-Isoindole-5-carboxylic acid,2,3-dihydro-2-methyl-7-[4-(methylsulfonyl)phenoxy]-3-oxo-,methyl esterYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A sealed tube was charged with a solution of dimethyl 4-formyl-5-(4-(methylsulfonyl)phenoxy)-isophthalate (210 mg, 0.535 mmol) in MeOH and aminomethane hydrochloride (72.3 mg, 1.07 mmol). After stirring the reaction at room temperature for 2 hours, NaCNBH3 (84.1 mg, 1.34 mmol) was added. The mixture was then stirred at 65° C. for 14 hours. The solvent was evaporated and replaced with ethyl acetate. The organic layer was then washed with brine (3×), dried over MgSO4, and concentrated. The crude sample was introduced into a silica gel column chromatography and eluted with 5-10% MeOH/CHCl3 to provide the desired product (100 mg, 50% yield) as white solid. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 3.09 (s, 3 H) 3.21 (s, 3 H) 3.94 (s, 3 H) 4.36 (s, 2 H) 7.07-7.21 (m, 2 H) 7.84 (d, J=1.13 Hz, 1 H) 7.90-8.03 (m, 2 H) 8.37 (d, J=1.13 Hz, 1 H); LC-MS (ESI)+m/z=376.00 (M+H)+.

Workup

  1. customthe reaction at room temperature for 2 hours
  2. stirringThe mixture was then stirred at 65° C. for 14 hours
  3. customThe solvent was evaporated
  4. washThe organic layer was then washed with brine (3×)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. additionThe crude sample was introduced into a silica gel column chromatography
  8. washeluted with 5-10% MeOH/CHCl3

Sources & evidence

ORD record
ord-10fc72f627ff405c857b7f6b73cf9b2e
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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