5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole → HCID 44561092, compound

HRID 1675517Notes

Reaction equation

HRID 1675517 reaction equation
Br[C:2]1[CH2:6][CH2:5][C:4](=[O:7])[C:3]=1[CH3:8].CC1(C)C(C)(C)OB([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][CH:21]=[CH:20]3)O1>>[NH:22]1[C:23]2[C:19](=[CH:18][C:17]([C:2]3[CH2:6][CH2:5][C:4](=[O:7])[C:3]=3[CH3:8])=[CH:25][CH:24]=2)[CH:20]=[CH:21]1

Participants

3

Reactant 2

HCID 27347725-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indoleHCID 112982573-bromo-2-methylcyclopent-2-enone

Product 1

HCID 44561092HCID 44561092, compoundYield 92%

Procedure

Synthesized from 3-bromo-2-methylcyclopent-2-enone and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole according to the general procedure described for the Suzuki coupling. Purification by automated flash chromatography using gradient elution (0 to 100% ethyl acetate/hexanes) and further recrystallization yielded the product (138 mg, 92%) as pale yellow solid. 1H NMR (CDCl3, 300 MHz): δ 7.86 (s, 1H), 7.47-7.39 (m, 2H), 7.27 (t, J=3.0 Hz, 1H), 6.62 (t, J=2.1 Hz, 1H), 3.02-2.97 (m, 2H), 2.57-2.54 (m, 2H), 2.05 (t, 3H, J=1.8). 13C NMR (CDCl3, 75 MHz): δ 210.0, 168.3, 136.2, 134.5, 128.2, 127.8, 125.3, 121.9, 120.6, 111.1, 103.4, 34.2, 29.7, 10.5. LCMS (ESI): mass calcd for (C14H13NO) m/z 211.10; measured [M+H]+: m/z 212.03.

Workup

  1. customPurification by automated flash chromatography
  2. washelution (0 to 100% ethyl acetate/hexanes) and further recrystallization

Sources & evidence

ORD record
ord-9e0af7f3cc60494a8ac760ba06d0f378
Source dataset
uspto-grants-2011_08
Patent number
US08003692B2

Reaction notes

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