Water → HCID 86618892, compound

HRID 1435774Notes

Reaction equation

HRID 1435774 reaction equation
[H-].[Na+].[N:3]([C@H:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C@H:8]([C:15]2[C:23]3[C:18](=[CH:19][C:20]([O:24][CH3:25])=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:7]1)=[N+:4]=[N-:5].[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1.O>C1COCC1.C(OCC)(=O)C>[N:3]([C@H:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C@H:8]([C:15]2[C:23]3[C:18](=[CH:19][C:20]([O:24][CH3:25])=[CH:21][CH:22]=3)[N:17]([S:32]([C:29]3[CH:30]=[CH:31][C:26]([CH3:36])=[CH:27][CH:28]=3)(=[O:34])=[O:33])[CH:16]=2)[CH2:7]1)=[N+:4]=[N-:5]

Participants

7

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 86618893HCID 86618893, compound

Product 1

HCID 86618892HCID 86618892, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

1 g Sodium hydride (60% in mineral oil) was added to 2 g 3-((1R,3R)-3-azido-indan-1-yl)-6-methoxy-1H-indole in 50 mL dry THF at 5° C. and the reaction mixture was stirred 1 hour at 5° C. 2 g p-toluene sulfonic acid chloride was added in portions at 5° C. and stirring was continued for another 4 hours. Ice was added and after 1 hour water and ethyl acetate was added. The organic phase was separated and washed with brine, dried over MgSO4 and concentrated in vacuo. After flash chromatography (heptane/ethyl acetate, silica gel), 2.5 g 3-((1R,3R)-3-azido-indan-1-yl)-6-methoxy-1-(toluene-4-sulfonyl)-1H-indole was isolated.

Workup

  1. stirringstirring
  2. waitwas continued for another 4 hours
  3. additionwas added
  4. customThe organic phase was separated
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5f6035f5d0f94e31af8bb1b9fb8dc4c2
Source dataset
uspto-grants-2009_11
Patent number
US07618967B2

Reaction notes

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