3-Pyridinylboronic acid → HCID 67516106, compound

HRID 1054062Notes

Reaction equation

HRID 1054062 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[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:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[N:20][CH:21]=2)[CH:14]=[CH:13][N:12]=[CH:11]1

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 67516106HCID 67516106, compound

Procedure

Synthesized using 3-pyridylboronic acid (206 mg, 1.68 mmol) and 1a (200 mg, 0.84 mmol) according to Method C. Yellow solid. Yield: 144 mg, 0.61 mmol, 73%. 1H NMR (CDCl3, 500 MHz): δH (ppm): 5.20 (s, 2H), 6.93 (t, J=1.5 Hz, 1H), 7.13 (t, J=0.9 Hz, 1H), 7.40 (ddd, J=7.9, 4.7, 0.9 Hz, 1H), 7.52 (dd, J=8.2, 2.2 Hz, 1H), 7.60 (s, 1H), 7.75 (d, J=8.2 Hz), 8.29-8.32 (m, 1H), 8.61 (m, 1H), 8.66 (dd, J=4.7, 1.5 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.0, 119.0, 120.6, 123.6, 130.5, 131.0, 134.0, 134.3, 135.9, 137.3, 148.2, 148.9, 150.3, 155.0. MS (ESI): m/z=237.03 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-e701fe54473047339c49bef380c7af6c
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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