Benzo(B)Thiophene-2-Boronic Acid → HCID 24747233, compound

HRID 1675502Notes

Reaction equation

HRID 1675502 reaction equation
Br[C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1.[S:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH:11]=[C:10]1B(O)O>>[S:9]1[C:10]([C:2]2[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=2)=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]1=2

Participants

3

Reactant 2

HCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 109650383-Bromocyclohex-2-enone

Product 1

HCID 24747233HCID 24747233, compoundYield 89%

Procedure

Synthesized from 3-bromocyclohex-2-enone and benzothiophene-2-boronic acid according to the general procedure described for the Suzuki coupling. Purification by automated flash chromatography yielded the product (134 mg, 89%) as a white solid. 1H NMR (300 MHz, CDCl3): δ 7.73-7.82 (m, 2H), 7.58 (s, 1H), 7.31-7.39 (m, 2H), 6.46 (s, 1H), 2.87 (td, J=5.9, 1.2 Hz, 2H), 2.51 (t, J=6.3 Hz, 2H), 2.18 (quintet, J=6.3 Hz, 2H). 13C (75 MHz, CDCl3): 199.3, 152.5, 142.6, 140.2, 139.8, 126.3, 125.04, 125.0, 124.9, 124.6, 122.5, 37.6, 27.9, 22.8. HRMS (LCT Electrospray): mass calcd for (C14H12OS+Na) m/z 251.0507; measured [M+Na]+: m/z 251.0501.

Workup

  1. customPurification by automated flash chromatography

Sources & evidence

ORD record
ord-63d5a93fcc38488cb1bc87bf98b0619e
Source dataset
uspto-grants-2011_08
Patent number
US08003692B2

Reaction notes

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