Furan-3-boronic acid → HCID 57329785, compound

HRID 1054074Notes

Reaction equation

HRID 1054074 reaction equation
[O:1]1[CH:5]=[CH:4][C:3](B(O)O)=[CH:2]1.[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][C:3]([C:18]2[CH:17]=[CH:16][C:15]([CH2:14][N:9]3[CH:13]=[CH:12][N:11]=[CH:10]3)=[CH:20][N:19]=2)=[CH:2]1

Participants

3

Reactant 2

HCID 2734358Furan-3-boronic acidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 57329785HCID 57329785, compound

Procedure

Synthesized using 3-furanylboronic acid (188 mg, 1.68 mmol) and 1a (200 mg, 0.84 mmol) according to Method C. Brown solid. Yield: 144 mg, 0.61 mmol, 73%. 1H NMR (CDCl3, 500 MHz): OH (ppm): 5.13 (s, 2H), 6.87 (dd, J=1.9, 0.9 Hz, 1H), 6.90 (t, J=1.3 Hz, 1H), 7.10 (s, 1H), 7.41 (dd, J=8.2, 2.2 Hz, 1H), 7.43 (dd, J=8.2, 1.3 Hz, 1H), 7.49 (t, J=1.6 Hz, 1H), 7.56 (brs, 1H), 8.02 (dd, J=0.7 Hz, J=1.4 Hz, 1H); 13C NMR (CDCl3, 125 MHz): 00 (ppm)=48.1, 108.5, 118.9, 120.1, 126.5, 129.5, 130.3, 135.6, 137.3, 141.5, 144.0, 148.6, 152.1; MS (ESI): m/z=226.15 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-b013e94b92cb4cdb95f4478f04ccaad6
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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