(5-Bromopentyl)benzene → HCID 11652690, compound

HRID 898178Notes

Reaction equation

HRID 898178 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][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[C:22]1([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:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 285561(5-Bromopentyl)benzeneHCID 59691753Methyl 5-(pyridin-2-yl)-1,3,4-oxadiazole-2-carboxylate

Product 1

HCID 11652690HCID 11652690, compoundYield 49%

Procedure

Starting with methyl 5-(pyridin-2-yl)-[1,3,4]-oxadiazole-2-carboxylate and 5-bromopentylbenzene, the title compound (21 mg, 49%) was obtained as a white solid, using a procedure similar to Example 1. 1H NMR (400 MHz, CDCl3) 1.45 (m, 2H), 1.68 (quintet, J=7.8 Hz, 2H), 1.86 (quintet, J=7.6 Hz, 2H), 2.62 (t, J=7.6 2H), 3.31 (t, J=7.5 Hz, 2H), 7.18-7.20 (m, 3H), 7.27-7.29 (m, 2H), 7.54 (d 7.9, 5.0, 1.2 Hz, 1H), 7.94 (td, J=7.6, 1.8 Hz, 1H), 8.30 (d, J=7.9 Hz, 1H), 8.85 (d, J=5.0 Hz, 1H); 13C NMR (CDCl3, 100 MHz) 23.4, 28.6, 31.1, 35.7, 40.0, 124.0, 125.7, 126.7, 128.3, 128.4, 137.3, 142.3, 142.6, 150.8, 161.2, 165.1, 187.0; MALDI-FTMS m/z 322.1557 (C19H19N3O2+H+ requires 322.1556).

Sources & evidence

ORD record
ord-c4e8a699f6c04c9ea2b1957de756de16
Source dataset
uspto-grants-2008_04
Patent number
US07351724B2

Reaction notes

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