(Pyridin-4-yl)boronic acid → HCID 67516855, compound

HRID 1054063Notes

Reaction equation

HRID 1054063 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.[N:10]1([CH2:15][C:16]2[CH:17]=[CH:18][C:19](Br)=[N:20][CH:21]=2)[CH:14]=[CH:13][N:12]=[CH:11]1>>[N:10]1([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)=[N:20][CH:21]=2)[CH:14]=[CH:13][N:12]=[CH:11]1

Participants

3

Reactant 2

HCID 2734379(Pyridin-4-yl)boronic acidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 67516855HCID 67516855, compound

Procedure

Synthesized using 4-pyridylboronic acid (123 mg, 1.00 mmol) and 1a (95 mg, 0.4 mmol) according to Method C. Yellow solid. Yield: 73 mg, 77%. 1H NMR (500 MHz, CDCl3): δH (ppm): 5.22 (s, 2H), 6.94 (t, J=1.3 Hz, 1H), 7.14 (brs, 1H), 7.54 (dd, J=2.5, 8.2 Hz, 1H), 7.60 (s, 1H), 7.80 (d, J=8.2 Hz, 1H), 7.88 (dd, J=1.6, 4.1 Hz, 2H), 8.64 (dd, J=0.6, 2.5 Hz, 1H), 8.73 (dd, J=1.6, 4.4 Hz, 2H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.3, 119.3, 121.2, 130.8, 132.3, 136.2, 137.6, 149.1, 150.8, 155.1; MS (ESI): m/z=237.02 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-5c504797e6e3425fbde7a6af6dabd94e
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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