Tetrabutylammonium Fluoride → HCID 67147466, compound

HRID 490426Notes

Reaction equation

HRID 490426 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]([CH2:14][CH2:15][CH2:16][O:17][Si](C(C)(C)C)(C)C)[CH:7]=[C:6]2[C:25]1[N:33]([S:34]([C:37]2[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=2)(=[O:36])=[O:35])[C:28]2=[N:29][CH:30]=[CH:31][CH:32]=[C:27]2[CH:26]=1.[F-:44].C([N+](CCCC)(CCCC)CCCC)CCC>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]([CH2:14][CH2:15][CH2:16][F:44])[CH:7]=[C:6]2[C:25]1[N:33]([S:34]([C:37]2[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=2)(=[O:36])=[O:35])[C:28]2=[N:29][CH:30]=[CH:31][CH:32]=[C:27]2[CH:26]=1.[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]([CH2:14][CH2:15][CH2:16][OH:17])[CH:7]=[C:6]2[C:25]1[N:33]([S:34]([C:37]2[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=2)(=[O:35])=[O:36])[C:28]2=[N:29][CH:30]=[CH:31][CH:32]=[C:27]2[CH:26]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67147461HCID 67147461, compound

Product 2

HCID 67147466HCID 67147466, compoundHCID 67147595HCID 67147595, compound

Procedure

3-{5,6-Dimethoxy-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]indol-1-yl}propanol and 2-[5,6-dimethoxy-1-(3-fluoropropyl)indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine are prepared by following the procedure described in example 89b, but using 0.605 g of 2-[5,6-dimethoxy-1-(3-tert-butyldimethylsilyloxypropyl)indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine and 1.95 ml of tetrabutylammonium fluoride (TBAF). After purification by flash chromatography (silica, 98/02 by volume dichloromethane/methanol as eluents, argon), 0.243 g of 3-{5,6-dimethoxy-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]indol-1-yl}propanol is obtained, the characteristics of which are as follows:

Workup

  1. customAfter purification by flash chromatography (silica, 98/02 by volume dichloromethane/methanol as eluents, argon)

Sources & evidence

ORD record
ord-d59c0a1ebfb64115939d5cd37bb7b0ce
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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