3-Bromo-5,5-dimethyl-2-cyclohexen-1-one → HCID 24747203, compound

HRID 1675514Notes

Reaction equation

HRID 1675514 reaction equation
Br[C:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[O:10])[CH:3]=1.[NH:11]1[C:19]2[C:14](=[CH:15][C:16](B3OC(C)(C)C(C)(C)O3)=[CH:17][CH:18]=2)[CH:13]=[CH:12]1>>[NH:11]1[C:19]2[C:14](=[CH:15][C:16]([C:2]3[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[O:10])[CH:3]=3)=[CH:17][CH:18]=2)[CH:13]=[CH:12]1

Participants

3

Reactant 2

HCID 1394173-Bromo-5,5-dimethyl-2-cyclohexen-1-oneHCID 27347725-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Product 1

HCID 24747203HCID 24747203, compoundYield 95%

Procedure

Synthesized from 3-Bromo-5,5-dimethyl-cyclohex-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 (0 to 80% ethyl acetate/hexanes) yielded the product (177 mg, 95%) as an off-white solid. 1H NMR (300 MHz, CDCl3): δ 8.97 (bs, 1H), 7.84 (s, 1H), 7.39 (d, J=1.2 Hz, 2H), 7.22 (dd, J=3.0, 2.1 Hz, 1H), 6.56 (dd, J=3.0, 2.1 Hz, 1H), 6.49 (t, J=1.5 Hz, 1H), 2.74 (d, J=1.2 Hz, 2H), 2.35 (s, 2H), 1.25 (s, 3H), 1.14 (s, 3H). 13C (75 MHz, CDCl3): 200.4, 159.5, 136.8, 130.2, 127.9, 125.5, 122.4, 120.1, 119.1, 111.3, 103.1, 50.9, 42.6, 33.8, 28.4, 24.9. HRMS (LCT Electrospray): mass calcd for (C16H17NO+Na) m/z 262.1208; measured [M+Na]+: m/z 262.1204.

Workup

  1. customPurification by automated flash chromatography
  2. washelution (0 to 80% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-5193702950f244dca093cafe7c2e98f5
Source dataset
uspto-grants-2011_08
Patent number
US08003692B2

Reaction notes

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