1-Ethynyl-4-propylbenzene → Ethyloxo{({3-[(4-propylphenyl)ethynyl]-1-benzofuran-5-yl}methyl)[4 (trifluoromethyl)benzyl]amino}acetate

HRID 735945Notes

Reaction equation

HRID 735945 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[C:5]([N:7]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]2[O:27][CH:26]=[C:25](Br)[C:24]=2[CH:29]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)=[O:6])[CH3:2].[C:31]([C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][CH3:41])=[CH:35][CH:34]=1)#[CH:32]>>[CH2:1]([O:3][C:4](=[O:30])[C:5](=[O:6])[N:7]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]2[O:27][CH:26]=[C:25]([C:32]#[C:31][C:33]3[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][CH3:41])=[CH:35][CH:34]=3)[C:24]=2[CH:29]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)[CH3:2]

Participants

3

Reactant 2

HCID 27751331-Ethynyl-4-propylbenzeneHCID 67188647Ethyl{[(3-bromo-1-benzofuran-5-yl)methyl)[4-(trifluoromethyl)benzyl]amino}(oxo)acetate

Product 1

HCID 67186980Ethyloxo{({3-[(4-propylphenyl)ethynyl]-1-benzofuran-5-yl}methyl)[4 (trifluoromethyl)benzyl]amino}acetateYield 5%

Procedure

The same procedure as employed in the preparation of Example 226 (step c) but using ethyl{[(3-bromo-1-benzofuran-5-yl)methyl][4-(trifluoromethyl)benzyl]amino}(oxo)acetate and 1-ethynyl-4-propylbenzene under microwave conditions (300 W, 120° C., 10 min) gave the title compound as a yellow oil (5%). M−(LC/MS(ESI)): 545.8; M+(LC/MS(ESI)): 548.2 HPLC (Condition A), Rt: 5.85 min (HPLC purity: 92.4%).

Workup

  1. customThe same procedure as employed in the preparation of Example 226 (step c)
  2. customunder microwave conditions (300 W, 120° C., 10 min)

Sources & evidence

ORD record
ord-64c1fa1ca3dd41dead922fbe6dda88ec
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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