4-Cyanophenylboronic acid → HCID 67515801, compound

HRID 1054056Notes

Reaction equation

HRID 1054056 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)#[N:2].[N:12]1([CH2:17][C:18]2[CH:19]=[CH:20][C:21](Br)=[N:22][CH:23]=2)[CH:16]=[CH:15][N:14]=[CH:13]1>>[N:12]1([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)=[N:22][CH:23]=2)[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

3

Reactant 2

HCID 27343264-Cyanophenylboronic acidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 67515801HCID 67515801, compound

Procedure

Synthesized using 4-cyanophenylboronic acid (185 mg, 1.26 mmol) and 1a (150 mg, 0.63 mmol) according to Method C. Yellow solid. Yield: 110 mg, 0.42 mmol, 67%. 1H NMR (CDCl3, 500 MHz): δH (ppm): 5.22 (s, 2H), 6.93 (s, 1H), 7.14 (s, 1H), 7.54 (dd, J=8.2, 2.3 Hz, 1H), 7.60 (s, 1H), 7.75-7.78 (m, 3H), 8.11 (d, J=8.2 Hz, 2H), 8.62 (s, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.0, 112.9, 118.6, 119.0, 121.0, 127.4, 130.5, 131.5, 132.6, 136.0, 137.3, 142.6, 148.8, 150.4; MS (ESI): m/z=261.03 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-d81042ca5ce0480eafbcab87ab9cfbd4
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

Loading…