2-(5-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-1-yl)ethanol → 2-(6-(4-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-1H-indol-1-yl)ethanol

HRID 331024Notes

Reaction equation

HRID 331024 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1B1OC(C)(C)C(C)(C)O1)[N:7]([CH2:20][CH2:21][OH:22])[CH:6]=[CH:5]2.[Br:23][C:24]1[CH:29]=[CH:28][N:27]=[C:26]2[N:30]([CH3:34])[CH:31]=[C:32](I)[C:25]=12>>[Br:23][C:24]1[CH:29]=[CH:28][N:27]=[C:26]2[N:30]([CH3:34])[CH:31]=[C:32]([C:10]3[CH:9]=[C:8]4[C:4]([CH:5]=[CH:6][N:7]4[CH2:20][CH2:21][OH:22])=[CH:3][C:2]=3[F:1])[C:25]=12

Participants

3

Reactant 2

HCID 710901092-(5-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-1-yl)ethanolHCID 710901484-bromo-3-iodo-1-methyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 867202882-(6-(4-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-1H-indol-1-yl)ethanol

Procedure

The title compound was prepared from 2-(5-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-1-yl)ethanol (D79) and 4-bromo-3-iodo-1-methyl-1H-pyrrolo[2,3-b]pyridine (D7) using a similar procedure to that described for D8. LCMS (A): m/z (M+H)+ 388/390, C18H15BrFN3O requires 387/389 (acidic).

Sources & evidence

ORD record
ord-f2d85cfd3af34acbb028f5f7ca4f9fcb
Source dataset
uspto-grants-2014_11
Patent number
US08877742B2

Reaction notes

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