(8-Bromooctyl)benzene → 9-Phenyl-1-(5-(pyridin-2-yl)-1,3,4-oxadiazol-2-yl)nonan-1-one

HRID 898180Notes

Reaction equation

HRID 898180 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][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[C:25]1([CH2:24][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:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 563758(8-Bromooctyl)benzeneHCID 59691753Methyl 5-(pyridin-2-yl)-1,3,4-oxadiazole-2-carboxylate

Product 1

HCID 116962469-Phenyl-1-(5-(pyridin-2-yl)-1,3,4-oxadiazol-2-yl)nonan-1-oneYield 43%

Procedure

Starting with methyl 5-(pyridin-2-yl)-[1,3,4]-oxadiazole-2-carboxylate and 8-bromooctylbenzene, the title compound (28 mg, 43%) was obtained as a white solid using a procedure similar to Example 1. 1H NMR (400 MHz, CDCl3) 1.34 (m, 8H), 1.62 (quintet, J=7.3 Hz, 2H), 1.81 (quintet, J=7.3 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 (dd, J=7.6, 4.7, Hz, 1H), 7.93 (td, J=7.6, 1.5 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, 29.00, 29.02, 29.2, 31.4, 35.90, 35.92, 40.1, 124.0, 125.5, 126.7, 128.2, 128.4, 137.3, 142.6, 142.8, 150.8, 161.2, 165.0, 187.2; MALDI-FTMS m/z 364.2024 (C22H25N3O2+H+ requires 364.2019).

Sources & evidence

ORD record
ord-6c817522da0f4ae6910c3469fd763be7
Source dataset
uspto-grants-2008_04
Patent number
US07351724B2

Reaction notes

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