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

HRID 735943Notes

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][CH3:40]>>[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][CH3:40])[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

Reactant 2

HCID 129971-Decyne

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

Product 1

HCID 67187736Ethyl{[(3-dec-1-ynyl-1-benzofuran-5-yl)methyl][4-(trifluoromethyl)-benzyl]amino}(oxo)acetateYield 40%

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-decyne gave the title compound as a yellow oil (40%). 1H NMR (CDCl3, 300 MHz) δ 7.78 (s, 0.5H), 7.76 (s, 0.5H), 7.65 (d, 1H, J=7.9 Hz), 7.61 (d, 1H, J=7.9 Hz), 7.52-7.33 (m, 4H), 7.22 (m, 1H), 4.64 (s, 1H), 4.56 (s, 1H), 4.47 (s, 1H), 4.41 (s, 1H), 4.39 (q, 1H, J=7.2 Hz), 4.34 (q, 1H, J=7.2 Hz), 2.49 (m, 2H), 1.66 (m, 2H), 1.49 (m, 2H), 1.40-1.26 (m, 11H), 0.89 (t, 3H, J=6.8 Hz). M−(LC/MS(ESI)): 540.5; M+(LC/MS(ESI)): 542.7. HPLC (Condition A), Rt: 6.07 min (HPLC purity: 98.0%).

Workup

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

Sources & evidence

ORD record: ord-437092e8a9b949ef90d283be27f296c9
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592477B2

Reaction notes

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