1-Bromo-7-phenylheptane → 8-Phenyl-1-(5-(pyridin-2-yl)-1,3,4-oxadiazol-2-yl)octan-1-one

HRID 898179Notes

Reaction equation

HRID 898179 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[O:11][C:10]([C:12]([O:14]C)=O)=[N:9][N:8]=1.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[C:24]1([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:12]([C:10]2[O:11][C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[N:8][N:9]=2)=[O:14])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 27356031-Bromo-7-phenylheptaneHCID 59691753Methyl 5-(pyridin-2-yl)-1,3,4-oxadiazole-2-carboxylate

Product 1

HCID 116959728-Phenyl-1-(5-(pyridin-2-yl)-1,3,4-oxadiazol-2-yl)octan-1-oneYield 41%

Procedure

Starting with methyl 5-(pyridin-2-yl)-[1,3,4]-oxadiazole-2-carboxylate and 7-bromoheptylbenzene, the title compound (25 mg, 41%) was obtained as a white solid, using a procedure similar to Example 1. 1H NMR (400 MHz, CDCl3) 1.38 (m, 6H), 1.63 (quintet, J=7.3 Hz, 2H), 1.80 (quintet, J=7.0 Hz, 2H), 2.61 (dd, J=7.9, 7.6 Hz, 2H), 3.21 (t, J=7.5 Hz, 2H), 7.16-7.19 (m, 3H), 7.26-7.30 (m, 2H), 7.54 (ddd, J=7.6, 4.7, 0.9 Hz, 1H), 7.94 (td, J=7.8,1.8 Hz, 1H), 8.30 (d, J=7.9 Hz, 1H), 8.85 (d, J=4.7 Hz, 1H); 13C NMR (CDCl3, 100 MHz) 23.6, 28.9, 29.0, 29.1, 31.4, 35.7, 35.9, 40.1, 124.0, 125.6, 126.7, 128.2, 128.4, 137.3, 142.6, 142.7, 150.8, 161.2, 165.1, 187.2; MALDI-FTMS m/z 350.1859 (C21H23N3O2+H+ requires 350.1863).

Sources & evidence

ORD record
ord-76a0eda48a874e0c8ec41f54c34920b1
Source dataset
uspto-grants-2008_04
Patent number
US07351724B2

Reaction notes

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