Water → HCID 69459893, compound

HRID 1351983Notes

Reaction equation

[OH:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[C:8]([OH:13])[CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH3:14][C@@:15]1(S([O-])(=O)=O)C=CC(C)=C(CC=O)[CH:16]1[N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.C(=O)([O-])[O-:36].[K+].[K+].O>CN(C)C=O>[CH3:14][C@H:15]([O:13][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[NH:6][CH:5]=[C:4]2[CH2:3][CH2:2][OH:1])[C:16]([N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)=[O:36]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 3-(2-hydroxyethyl)-1H-indol-7-ol (1.05 g, 5.93 mmol) in N,N-dimethylformamide (20 mL) are added (1R)-1-methyl-2-morpholin-4-yl-2-oxoethyl-4-methylbenzenesulfonate (2.79 g, 8.90 mmol) and potassium carbonate (1.3 g, 9.41 mmol), and the mixture is stirred at 60° C. for 5 hours. The reaction solution is cooled to room temperature, and the mixture is poured into water. The mixture is extracted with ethyl acetate, and the organic layer is washed with a saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous sodium sulfate. The solvent is removed by distillation, and the obtained crude product is purified by silica gel column chromatography (chloroform→chloroform:methanol=50:1→30:1) to give the title compound (1.29 g, yield: 68%).

Workup

temperatureThe reaction solution is cooled to room temperature
extractionThe mixture is extracted with ethyl acetate
washthe organic layer is washed with a saturated aqueous sodium hydrogen carbonate solution
dry with materialdried over anhydrous sodium sulfate
customThe solvent is removed by distillation
customthe obtained crude product
customis purified by silica gel column chromatography (chloroform→chloroform:methanol=50:1→30:1)

Sources & evidence

ORD record: ord-3ee54c12e81d4d98a9187949e037a901
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07217724B2

Reaction notes

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