Furan-2-boronic acid → 2,3-Di-furan-2-yl-5-imidazol-1-ylmethyl-pyridine

HRID 1054076Notes

Reaction equation

HRID 1054076 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1B(O)O.Br[C:10]1[C:11](Cl)=[N:12][CH:13]=[C:14]([CH2:16][N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)[CH:15]=1>>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:11]1[C:10]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[CH:15][C:14]([CH2:16][N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)=[CH:13][N:12]=1

Participants

3

Reactant 2

HCID 2734357Furan-2-boronic acidHCID 706831103-Bromo-2-chloro-5-imidazol-1-ylmethyl-pyridine

Product 1

HCID 573297862,3-Di-furan-2-yl-5-imidazol-1-ylmethyl-pyridine

Procedure

Synthesized using 2-furanylboronic acid (123 mg, 1.10 mmol) and 6 (150 mg, 0.55 mmol) according to Method C. Yellow solid. Yield: 108 mg, 0.37 mmol, 67%. 1H NMR (500 MHz, CDCl3): δH (ppm): 5.19 (s, 2H), 6.26 (dd, J=3.5, 0.6 Hz, 1H), 6.41 (dd, J=3.5, 0.9 Hz, 1H), 6.41-6.48 (m, 2H), 6.93 (t, J=1.3 Hz, 1H), 7.12 (bs, 1H), 7.49-7.50 (m, 2H), 7.60 (bs, 1H), 7.61 (d, J=2.2 Hz, 1H), 8.50 (d, J=2.2 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=47.9, 110.0, 111.6, 111.7, 111.7, 119.0, 124.8, 130.0, 130.4, 136.0, 137.3, 142.8, 143.3, 146.8, 147.4, 149.9, 151.7; MS (ESI): m/z=292.09 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-539374bcd9c944c490c4d4cbe92f5f53
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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