Furan-2-boronic acid → HCID 67510362, compound

HRID 1054073Notes

Reaction equation

HRID 1054073 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1B(O)O.[N:9]1([CH2:14][C:15]2[CH:16]=[CH:17][C:18](Br)=[N:19][CH:20]=2)[CH:13]=[CH:12][N:11]=[CH:10]1>>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:18]1[CH:17]=[CH:16][C:15]([CH2:14][N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)=[CH:20][N:19]=1

Participants

3

Reactant 2

HCID 2734357Furan-2-boronic acidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 67510362HCID 67510362, compound

Procedure

Synthesized using 2-furanylboronic acid (141 mg, 1.26 mmol) and 1a (150 mg, 0.63 mmol) according to Method C. Yellow solid. Yield: 127 mg, 0.56 mmol, 89%. 1H NMR (CDCl3, 500 MHz): δH (ppm): 5.12 (s, 2H), 6.52 (dd, J=3.4, 1.5 Hz, 1H), 6.89 (t, J=1.2 Hz, 1H), 7.05 (dd, J=3.4, 0.6 Hz, 1H). 7.09 (brs, 1H), 7.43 (dd, J=8.2, 2.1 Hz, 1H), 7.52 (dd, J=1.5, 0.6 Hz, 1H), 7.56 (s, 1H), 7.65 (d, J=8.2 Hz, 1H), 8.46 (d, J=1.8 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.1, 109.2, 112.1, 118.6, 118.9, 129.7, 130.2, 135.6, 137.2, 143.6, 148.4, 149.5, 152.9; MS (ESI): m/z=225.93 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-74a563522a914b528ba52714920b649c
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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