Ethanol → 5-(1-(ethyloxy)-2-{4-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)-4-methyl-2-benzofuran-1(3H)-one

HRID 1187109Notes

Reaction equation

HRID 1187109 reaction equation
[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH:12]1[CH2:14][O:13]1.[F:15][CH:16]([C:24]1[CH:33]=[CH:32][C:27]2[C:28](=[O:31])[O:29][CH2:30][C:26]=2[C:25]=1[CH3:34])[CH2:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.[CH2:35]([OH:37])[CH3:36]>>[F:15][CH:16]([C:24]1[CH:33]=[CH:32][C:27]2[C:28](=[O:31])[O:29][CH2:30][C:26]=2[C:25]=1[CH3:34])[CH2:17][N:18]1[CH2:23][CH2:22][N:21]([CH2:14][CH:12]([OH:13])[C:3]2[CH:4]=[CH:5][C:6]3[C:7](=[O:11])[O:8][CH2:9][C:10]=3[C:2]=2[CH3:1])[CH2:20][CH2:19]1.[CH2:35]([O:37][CH:16]([C:24]1[CH:33]=[CH:32][C:27]2[C:28](=[O:31])[O:29][CH2:30][C:26]=2[C:25]=1[CH3:34])[CH2:17][N:18]1[CH2:23][CH2:22][N:21]([CH2:14][CH:12]([OH:13])[C:3]2[CH:4]=[CH:5][C:6]3[C:7](=[O:11])[O:8][CH2:9][C:10]=3[C:2]=2[CH3:1])[CH2:20][CH2:19]1)[CH3:36]

Participants

5

Reactant 3

HCID 702EthanolHCID 552705554-methyl-5-(oxiran-2-yl)isobenzofuran-1(3H)-oneHCID 595686975-(1-fluoro-2-piperazin-1-ylethyl)-4-methyl-2-benzofuran-1(3H)-one

Product 2

HCID 498047735-(1-(ethyloxy)-2-{4-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)-4-methyl-2-benzofuran-1(3H)-oneHCID 498047745-(1-fluoro-2-{4-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)-4-methyl-2-benzofuran-1(3H)-one

Conditions

Temperature
150 °C

Procedure

4-Methyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one (75 mg, 0.394 mmol, 1.2 mmol) and 5-(1-fluoro-2-piperazin-1-ylethyl)-4-methyl-2-benzofuran-1(3H)-one (90 mg, 0.323 mmol, 1.0 eq) were suspended in ethanol (30 ml). The mixture was heated to 150° C. for 30 min under microwave irradiation. The mixture was concentrated and purify by flash column chromatograph (0-10% MeOH/DCM) to afford the expected product 5-(1-fluoro-2-{4-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)-4-methyl-2-benzofuran-1(3H)-one as well as byproduct 5-(1-(ethyloxy)-2-{4-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)-4-methyl-2-benzofuran-1(3H)-one.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurify by flash column chromatograph (0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-1fa24a7c362d4f05857327b70ef56b0a
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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