Cesium carbonate → N-[3-(Phenoxypropoxy)-4-methoxybenzenesulphonyl]-1,2-dihydroindole

HRID 2143

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([S:10]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14]2)(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[O:22]([CH2:29][CH2:30][CH2:31]Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[O:22]([CH2:29][CH2:30][CH2:31][O:1][C:2]1[CH:3]=[C:4]([S:10]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14]2)(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A solution of N-(3-hydroxy-4-methoxybenzenesulphonyl)- 1,2-dihydroindole (0.2 g) and 3-phenoxypropylbromide (0.15 g) in N,N-dimethylformamide (20 ml) was treated with cesium carbonate (0.3 g) and heated at 75° C. overnight. The solvent was removed in vacuo and the residue partitioned between dichloromethane (30 ml) and water (15 ml). The organic phase was washed with brine (15 ml) then dried over magnesium sulphate and concentrated in vacuo. The residue was purified using column chromatography eluting with dichloromethane to yield the title compound as a white solid (0.25 g).

Workup

customThe solvent was removed in vacuo
customthe residue partitioned between dichloromethane (30 ml) and water (15 ml)
washThe organic phase was washed with brine (15 ml)
dry with materialthen dried over magnesium sulphate
concentrationconcentrated in vacuo
customThe residue was purified
washeluting with dichloromethane

Sources & evidence

ORD record: ord-44bcaad266d04c4ebb5e17cd00e7e878
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05728712

Linked notes

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