(6-Bromohexyl)benzene → HCID 11674428, compound

HRID 898182Notes

Reaction equation

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

Participants

Reactant 2

HCID 561788(6-Bromohexyl)benzene

HCID 59691754HCID 59691754, compound

Product 1

HCID 11674428HCID 11674428, compoundYield 34%

Procedure

Starting with methyl 5-(pyridin-3-yl)-[1,3,4]-oxadiazole-2-carboxylate and 6-bromohexylbenzene, the title compound (20 mg, 34%) was obtained as a white solid, using a procedure analogous to that described in Example 1. 1H NMR (400 MHz, CDCl3) 1.44 (m, 4H), 1.66 (quintet, J=7.5 Hz, 2H), 1.82 (quintet, J=7.3 Hz, 2H), 2.63 (dd, J=7.9, 7.3 Hz, 2H), 3.21 (t, J=7.4 Hz, 2H), 7.17-7.19 (m, 3H), 7.26-7.30 (m, 2H), 7.52 (ddd, J=7.9, 4.7, 0.6 Hz, 1H), 7.94 (dt, J=7.9, 1.9 Hz, 1H) 8.85 (dd, J=5.0, 1.8 Hz, 1H), 9.41 (d, J=1.8 Hz, 1H); 13C NMR (CDCl3, 100 MHz) 23.6, 28.8, 28.9, 31.2, 35.8, 35.9, 40.0, 119.4, 123.9, 125.6, 128.2, 128.4, 134.9, 142.6, 148.7, 153.4, 161.0, 164.3, 187.3; MALDI-FTMS m/z 336.1716 (C20H21N3O2+H+ requires 336.1706).

Sources & evidence

ORD record: ord-5ac55eeaf4594610ae1f38fac6596fe3
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351724B2

Reaction notes

Loading…