Cyclopropylboronic acid → 7-Cyclopropyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

HRID 1993235Notes

Reaction equation

HRID 1993235 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:15]=2[NH:14][C:13]([B:16]2[O:20][C:19]([CH3:22])([CH3:21])[C:18]([CH3:24])([CH3:23])[O:17]2)=[CH:12]3)C=CC=[CH:3][CH:2]=1.C1(B(O)O)CC1>>[CH:1]1([C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:15]=2[NH:14][C:13]([B:16]2[O:20][C:19]([CH3:21])([CH3:22])[C:18]([CH3:23])([CH3:24])[O:17]2)=[CH:12]3)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 2760897Cyclopropylboronic acidHCID 59133116HCID 59133116, compound

Product 1

HCID 591331157-Cyclopropyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Procedure

Prepared according to the procedures described above for 7-phenyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole using cyclopropylboronic acid in place of phenylboronic acid. 1H NMR (CDCl3, 400 MHz): δ 0.75-0.82 (m, 2H), 0.95-1.04 (m, 2H), 2.08 (m, 1H), 6.59 (dd, J=3.0, 2.0 Hz, 1H), 6.96 (d, J=7.1 Hz, 1H), 7.06 (t, J=7.6 Hz, 1H), 7.25 (m, 1H), 7.52 (d, J=7.8 Hz, 1H) and 8.39 (br s, 1H) ppm. LC-MS (ES, Pos.): 158 [MH+].

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-233e3a481d3247d3927e4e548e070fd6
Source dataset
uspto-grants-2010_01
Patent number
US07651687B2

Reaction notes

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