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

HRID 2143
Notes
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Reaction equation

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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 68522Benzene, (3-bromopropoxy)-HCID 19689638N-(3-Hydroxy-4-methoxybenzenesulphonyl)-1,2-dihydroindole

Product 1

HCID 54309137N-[3-(Phenoxypropoxy)-4-methoxybenzenesulphonyl]-1,2-dihydroindoleYield 86.8%

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

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

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between dichloromethane (30 ml) and water (15 ml)
  3. washThe organic phase was washed with brine (15 ml)
  4. dry with materialthen dried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified
  7. 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

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes