4-Cyanophenylboronic acid → 1-[2-(4-Cyanophenyl)cyclopenten-1-yl]-4-(methylthio)benzene

HRID 2226000Notes

Reaction equation

HRID 2226000 reaction equation
Br[C:2]1[CH2:6][CH2:5][CH2:4][C:3]=1[C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1.[C:15]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)#[N:16]>>[C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:2]2[CH2:6][CH2:5][CH2:4][C:3]=2[C:7]2[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=2)=[CH:19][CH:18]=1)#[N:16]

Participants

3

Reactant 2

HCID 27343264-Cyanophenylboronic acidHCID 102650591-(2-Bromocyclopenten-1-yl)-4-(methylthio)benzene

Product 1

HCID 229173631-[2-(4-Cyanophenyl)cyclopenten-1-yl]-4-(methylthio)benzeneYield 89%

Procedure

Following the synthetic procedure outlined in Step 3 of Example 1, 500 mg (1.9 mmol) of 1-(2-bromocyclopenten-1-yl)-4-(methylthio) benzene (Example 1, Step 2) was reacted with 540 mg (3.7 mmol) of 4-cyanophenylboronic acid (Step 1). Purification by silica gel chromatography (MPLC) with hexane/ethyl acetate (19:1) gave 480 mg (89%) of 1-[2-(4-cyanophenyl)cyclopenten-1-yl]-4-(methylthio)benzene as an oil: NMR (CDCl3) d 2.07 (m, J=7 Hz, 2H) , 2.42 (s, 3H) , 2.89 (t, J=7 Hz, 4H) , 7.05 (d, J=8 Hz, 2H) , 7.11 (d, J=8 Hz, 2H) , 7 . 26 (d, J=8 Hz, 2H) , 7.48 (d, J=8 Hz, 2H ) .

Workup

  1. customPurification by silica gel chromatography (MPLC) with hexane/ethyl acetate (19:1)

Sources & evidence

ORD record
ord-c11669f65e8b48c79a6dca124f740c5e
Source dataset
uspto-grants-1994_09
Patent number
US05344991

Reaction notes

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