3-Bromo-1-propanol → 3-[6-(3-Hydroxy-propylamino)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one

HRID 1263720Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][O:7][C:8]2=[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]2=[O:20])=[CH:4][CH:3]=1.Br[CH2:22][CH2:23][CH2:24][OH:25]>CN(C=O)C.S([O-])([O-])(=O)=O.[Ag+2]>[OH:25][CH2:24][CH2:23][CH2:22][NH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][O:7][C:8]2=[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]2=[O:20])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 3-(6-Amino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (25.0 mg, 0.095 mmol), 3-bromo-1-propanol (85.5 μL, 0.946 mmol), and silver sulfate (59.0 mg, 0.189 mmol) in 0.8 mL DMF was heated at 120° C. for 1.5 h. The mixture was partitioned between EtOAc and H2O and the organic layer separated from the silver salts. The solution was washed with H2O, brine and then dried with Na2SO4. Concentrating the solution in vacuo gave a residue which was purified by chromatography (silica gel, CHCl3/MeOH, 96:4) to give the title compound (3 mg, 10%) as a yellow solid.

Workup

customThe mixture was partitioned between EtOAc and H2O
customthe organic layer separated from the silver salts
washThe solution was washed with H2O, brine
dry with materialdried with Na2SO4
concentrationConcentrating the solution in vacuo
customgave a residue which
customwas purified by chromatography (silica gel, CHCl3/MeOH, 96:4)

Sources & evidence

ORD record: ord-12d4b532942545549c39f396e2ae1b8c
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06541504B1

Reaction notes

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