(4-Methoxyphenyl)boronic acid → HCID 44456190, compound

HRID 1054049Notes

Reaction equation

HRID 1054049 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[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]([O:2][CH3:1])=[CH:4][CH:5]=3)=[N:22][CH:23]=2)[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

3

Reactant 2

HCID 201262(4-Methoxyphenyl)boronic acidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 44456190HCID 44456190, compound

Procedure

Synthesized using 4-methoxyphenylboronic acid (380 mg, 3.35 mmol) and 1a (400 mg, 1.68 mmol) according to Method C. Yellow solid. Yield: 400 mg, 1.51 mmol, 90%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=3.86 (s, 3H), 5.16 (s, 2H), 6.92 (t, J=1.3 Hz, 1H), 6.99 (d, J=9.1 Hz, 2H), 7.11 (s, 1H), 7.46 (dd, J=8.2, 2.5 Hz, 1H), 7.59 (s, 1H), 7.66 (d, J=8.2 Hz, 1H), 7.94 (d, J=9.1 Hz, 2H), 8.54 (d, J=2.5 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.1, 55.4, 114.2, 119.0, 119.8, 128.2, 129.2, 130.3, 131.2, 135.7, 137.3, 148.5, 157.4, 160.8; MS (ESI): m/z=266.22 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-a26637598a1b421bb3a90f23eca61a9d
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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