5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole → HCID 24747267, compound

HRID 1675511Notes

Reaction equation

HRID 1675511 reaction equation
Br[C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1.[NH:9]1[C:17]2[C:12](=[CH:13][C:14](B3OC(C)(C)C(C)(C)O3)=[CH:15][CH:16]=2)[CH:11]=[CH:10]1>>[NH:9]1[C:17]2[C:12](=[CH:13][C:14]([C:2]3[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=3)=[CH:15][CH:16]=2)[CH:11]=[CH:10]1

Participants

3

Reactant 2

HCID 27347725-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indoleHCID 109650383-Bromocyclohex-2-enone

Product 1

HCID 24747267HCID 24747267, compoundYield 83%

Procedure

Synthesized from 3-bromocyclohex-2-enone and indole-5-boronic acid pinacol ester according to the general procedure described for the Suzuki coupling. Purification by automated flash chromatography using gradient elution yielded the product (151 mg, 83%) as a pale yellow solid. 1H NMR (300 MHz, CDCl3): δ 8.68 (bs, 1H), 7.86 (d, J=0.3 Hz, 1H), 7.37-7.44 (m, 2H), 7.25 (dd, J=3.3, 2.5 Hz, 1H), 6.59 (t, J=2.5 Hz, 1H), 6.51 (t, J=1.1 Hz, 1H), 2.88 (td, J=6.3, 1.4 Hz, 2H), 2.51 (t, J=6.3 Hz, 2H), 2.18 (quintet, J=6.0 Hz, 2H). 13C (75 MHz, CDCl3): 200.1, 161.5, 136.7, 130.1, 127.9, 125.4, 123.7, 120.2, 119.1, 111.3, 103.3, 37.3, 28.5, 23.0. HRMS (LCT Electrospray): mass calcd for (C14H13NO+Na) m/z 234.0895; measured [M+Na]+: m/z 234.0897.

Workup

  1. customPurification by automated flash chromatography
  2. washelution

Sources & evidence

ORD record
ord-efc46a0b593a4aafadad5f6121df3733
Source dataset
uspto-grants-2011_08
Patent number
US08003692B2

Reaction notes

Loading…