2-Methoxyphenylboronic acid → 5-Imidazol-1-ylmethyl-2-(2-methoxy-phenyl)pyridine

HRID 1054048Notes

Reaction equation

HRID 1054048 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O.[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:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])=[N:22][CH:23]=2)[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

3

Reactant 2

HCID 27339582-Methoxyphenylboronic acidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 444561885-Imidazol-1-ylmethyl-2-(2-methoxy-phenyl)pyridine

Procedure

Synthesized using 2-methoxyphenylboronic acid (190 mg, 1.68 mmol) and 1a (200 mg, 0.84 mmol) according to Method C. Yellow solid. Yield: 210 mg, 0.79 mmol, 94%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=3.85 (s, 3H), 5.17 (s, 2H), 6.95 (brs, 1H), 7.00 (dd, J=8.5, 0.6 Hz, 1H), 7.08 (dt, J=7.6, 1.1 Hz, 1H), 7.12 (s, 1H), 7.38 (ddd, J=8.5, 7.6, 1.9 Hz, 1H), 7.44 (dd, J=8.5, 2.2 Hz, 1H), 7.60 (s, 1H), 7.77 (dd, J=7.6, 1.9 Hz, 1H), 7.83 (d, J=8.2 Hz, 1H), 8.60 (d, J=1.6 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.2, 55.6, 111.4, 119.1, 121.1, 125.2, 128.3, 129.5, 130.2, 130.3, 131.1, 134.6, 137.3, 148.2, 156.4, 157.0; MS (ESI): m/z=266.28 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-18824705edd349008a2c0990893a53e5
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

Loading…