1-Dodecyne → Ethyl{[(3-dodec-1-ynyl-1-benzofuran-5-yl)methyl][4-(trifluoromethyl)-benzyl]amino}(oxo)acetate

HRID 735944Notes

Reaction equation

HRID 735944 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].[CH:31]#[C:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]>>[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]([C:31]#[C:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[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]

Participants

3

Reactant 2

HCID 698211-DodecyneHCID 67188647Ethyl{[(3-bromo-1-benzofuran-5-yl)methyl)[4-(trifluoromethyl)benzyl]amino}(oxo)acetate

Product 1

HCID 67186391Ethyl{[(3-dodec-1-ynyl-1-benzofuran-5-yl)methyl][4-(trifluoromethyl)-benzyl]amino}(oxo)acetateYield 34%

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-dodecyne gave the title compound as a yellow oil (34%). HPLC (Condition A), Rt: 6.39 min (HPLC purity: 99.2%).

Workup

  1. customThe same procedure as employed in the preparation of Example 226 (step c)

Sources & evidence

ORD record
ord-06b50517024342928f17c0b3018371f6
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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