Allyl bromide → HCID 66886373, compound

HRID 76905Notes

Reaction equation

HRID 76905 reaction equation
[CH:1]1[N:2]=[CH:3][N:4]2[CH:9]([C:10]3[C:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:14][C:13]([C:22]#[N:23])=[CH:12][CH:11]=3)[CH2:8][CH2:7][CH2:6][C:5]=12.[CH2:24](Br)[CH:25]=[CH2:26]>>[CH2:26]([C:9]1([C:10]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:14][C:13]([C:22]#[N:23])=[CH:12][CH:11]=2)[N:4]2[CH:3]=[N:2][CH:1]=[C:5]2[CH2:6][CH2:7][CH2:8]1)[CH:25]=[CH2:24]

Participants

3

Reactant 2

HCID 7841Allyl bromideHCID 588270486-(5,6,7,8-Tetrahydroimidazo[1,5-a]pyridin-5-yl)biphenyl-3-carbonitrile

Product 1

HCID 66886373HCID 66886373, compound

Procedure

6-(5-Allyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine-5-yl)biphenyl-3-carbonitrile is prepared from 6-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)biphenyl-3-carbonitrile and allyl bromide by analogy to 19A above. MS (ESI) m/z 340 (M+H); 1H NMR (400 MHz, CDCl3) δ ppm (HCl salt) 1.73-1.98 (m, 2H), 2.02-2.16 (m, 1H), 2.23-2.38 (m, 1H), 2.54-2.65 (m, 1H), 2.68-2.83 (m, 1H), 2.86-3.02 (m, 1H), 3.00-3.14 (m, 1H), 5.11 (d, J=17.2 Hz, 1H), 5.23 (d, J=10.1 Hz, 1H), 5.44-5.69 (m, 1H), 6.87 (d, J=7.3 Hz, 1H), 6.92 (s, 1H), 7.02-7.12 (m, 1H), 7.13-7.22 (m, 1H), 7.27-7.39 (m, 3H), 7.45 (d, J=2.0 Hz, 1H), 7.71 (dd, J=8.5, 1.9 Hz, 1H), 8.31 (s, 1H).

Sources & evidence

ORD record
ord-d91a6dd18e484ff6bcf3dc8e64819cee
Source dataset
uspto-grants-2014_09
Patent number
US08835646B2

Reaction notes

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