Benzene, 1-chloro-4-ethynyl- → 4-[(4-chlorophenyl)ethynyl]-N-(3-cyclopentylpropyl)-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-7-yl)benzamide

HRID 551994Notes

Reaction equation

HRID 551994 reaction equation
Br[C:2]1[CH:31]=[CH:30][C:5]([C:6]([N:8]([CH2:22][CH2:23][CH2:24][CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[C:9]2[CH:10]=[CH:11][C:12]3[C:17](=[O:18])[O:16][C:15]([CH3:20])([CH3:19])[O:14][C:13]=3[CH:21]=2)=[O:7])=[CH:4][CH:3]=1.[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]#[CH:40])=[CH:35][CH:34]=1>>[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]#[C:40][C:2]2[CH:3]=[CH:4][C:5]([C:6]([N:8]([CH2:22][CH2:23][CH2:24][CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[C:9]3[CH:10]=[CH:11][C:12]4[C:17](=[O:18])[O:16][C:15]([CH3:20])([CH3:19])[O:14][C:13]=4[CH:21]=3)=[O:7])=[CH:30][CH:31]=2)=[CH:35][CH:34]=1

Participants

3

Reactant 2

HCID 70118Benzene, 1-chloro-4-ethynyl-HCID 575545704-bromo-N-(3-cyclopentylpropyl)-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-7-yl)benzamide

Product 1

HCID 575544754-[(4-chlorophenyl)ethynyl]-N-(3-cyclopentylpropyl)-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-7-yl)benzamideYield 80%

Procedure

The title compound was prepared following procedure described in example 26, step d) from 4-bromo-N-(3-cyclopentylpropyl)-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-7-yl)benzamide (437 mg, 0.90 mmol) and 4-chlorophenylacetylene (Apollo, 118 mg, 0.86 mmol). Purification by flash chromatography on silicagel (EtOAc/c-Hex 20:80) gave 373 mg (80%) of the title compound as a white foam. HPLC, Rt: 6.03 min (purity: 93.6%). LC/MS, M+(ESI): 541.9. 1H NMR (CDCl3) δ: 7.78 (d, J=8.3 Hz, 1H), 7.24-7.45 (m, 8H), 6.74 (dd, J=8.4, 2.0 Hz, 1H), 6.58 (d, J=1.9 Hz, 1H), 3.90 (t, J=7.6 Hz, 2H), 1.46-1.86 (m, 9H), 1.40 (s, 6H), 1.36 (m, 2H), 1.03 (m, 2H).

Workup

  1. customThe title compound was prepared following procedure
  2. customPurification by flash chromatography on silicagel (EtOAc/c-Hex 20:80)

Sources & evidence

ORD record
ord-2688c08024ea480182baa7c3c5a5497a
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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