Acetaldehyde → 3-(5-Ethylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one

HRID 1829003Notes

Reaction equation

HRID 1829003 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[C:11]1[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]1=[O:20])[O:6][CH2:5]2.[CH:21](=O)[CH3:22].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH2:21]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[C:11]1[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]1=[O:20])[O:6][CH2:5]2)[CH3:22]

Participants

4

Reactant 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 696596273-(5-Amino-2-benzofuran-1(3H)-ylidene)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 696602193-(5-Ethylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-oneYield 25.5%

Procedure

A mixture of 3-(5-Amino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (50.0 mg, 0.189 mmol), acetaldehyde (10.0 mg, 0.227 mmol), and sodium triacetoxyborohydride (52.1 mg, 0.246 mmol) was stirred at room temperature for 50.5 h. The reaction was then partitioned between EtOAc and H2O. The organic phase was washed with H2O, brine and then dried with Na2SO4. The solvent was removed in vacuo and the solid chromatographed (CHCl3/MeOH, 97.5:2.5) to afford the title compound (14.1 mg, 25%) as a yellow solid.

Workup

  1. customThe reaction was then partitioned between EtOAc and H2O
  2. washThe organic phase was washed with H2O, brine
  3. dry with materialdried with Na2SO4
  4. customThe solvent was removed in vacuo
  5. customthe solid chromatographed (CHCl3/MeOH, 97.5:2.5)

Sources & evidence

ORD record
ord-9f61c20ba6b445cf8241ad644dc6576c
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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