5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole → 5-(2-chloro-6-fluorophenyl)-1H-indole

HRID 1529315Notes

Reaction equation

HRID 1529315 reaction equation
Br[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[Cl:9].CC1(C)C(C)(C)OB([C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[NH:23][CH:22]=[CH:21]3)O1>>[Cl:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=1[C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[CH:21]2

Participants

3

Reactant 2

HCID 27347725-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indoleHCID 219386602-Bromo-1-chloro-3-fluorobenzene

Product 1

HCID 679595775-(2-chloro-6-fluorophenyl)-1H-indoleYield 62.7%

Procedure

This title compound was prepared analogously to compound 25b using 2-bromo-1-chloro-3-fluorobenzene (39.5 g, 0.19 mol) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (37.0 g, 0.15 mol). The title compound (23.1 g, 62%) was obtained. MS (ESI, m/z): 246.0 (M+1).

Sources & evidence

ORD record
ord-5fe44c73f4df4e1a99677bfd7c0146ae
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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