Potassium Carbonate → 6-[3-(1,3,3-Trimethyl-2-oxo-2,3-dihydro-1H-indol-6-yloxymethyl)-phenyl]-hexanoic Acid Methyl Ester

HRID 2117211Notes

Reaction equation

[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:14])([CH3:13])[C:7](=[O:12])[N:8]2C)=[CH:4][CH:3]=1.[CH3:15][O:16][C:17](=[O:31])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29]Br)[CH:24]=1.[C:32](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:15][O:16][C:17](=[O:31])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]([O:1][C:2]2[CH:10]=[C:9]3[C:5]([C:6]([CH3:13])([CH3:14])[C:7](=[O:12])[NH:8]3)=[CH:4][CH:3]=2)[CH3:32])[CH:24]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 6-hydroxy-1,3,3-trimethyl-1,3-dihydro-indol-2-one (396 mg, 2.07 mmol) in DMF (7.6 mL) is added 6-(3-Bromomethyl-phenyl)-hexanoic acid methyl ester (682 mg, 2.28 mmol) and potassium carbonate (315 mg, 2.28 mmol). The resulting mixture is heated to 60° C., stirred for 2 hrs. then cooled to room temp and diluted with EtOAc. The organic layer is washed with water, brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (eluting with 30% ethyl acetate/hexanes) to give 352 mg of title compound. MS (ESI) 410 (M+H)+.

Workup

temperaturethen cooled to room temp
washThe organic layer is washed with water, brine
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue is purified by flash chromatography (eluting with 30% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-1f9c2abdb31a4f8dbda1ada84dabcb22
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE040558E1

Reaction notes

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