2-Thiopheneboronic acid → 3-Imidazol-1-ylmethyl-2-thiophen-2-yl-pyridine

HRID 1054070Notes

Reaction equation

HRID 1054070 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1B(O)O.Br[C:10]1[C:15]([CH2:16][N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)=[CH:14][CH:13]=[CH:12][N:11]=1>>[N:17]1([CH2:16][C:15]2[C:10]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:21]=[CH:20][N:19]=[CH:18]1

Participants

3

Reactant 2

HCID 27339602-Thiopheneboronic acidHCID 573298662-Bromo-3-imidazol-1-ylmethyl-pyridine

Product 1

HCID 573297933-Imidazol-1-ylmethyl-2-thiophen-2-yl-pyridine

Procedure

Synthesized using 2-thiophenylboronic acid (161 mg, 1.26 mmol) and 5 (150 mg, 0.63 mmol) according to Method C. Yellow solid. Yield: 111 mg, 0.46 mmol, 73%. 1H NMR (500 MHz, CDCl3): δH (ppm): 5.39 (s, 2H), 6.88 (t, J=1.3 Hz, 1H), 7.13-7.15 (m, 2H), 7.17 (dd, J=7.9, 1.9 Hz, 1H), 7.20 (dd, J=7.9, 4.4 Hz, 1H), 7.23 (dd, J=3.8, 1.3 Hz, 1H), 7.50 (dd, J=5.0, 1.3 Hz, 1H), 7.51 (brs, 1H). 8.60 (dd, J=4.4, 1.9 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.4, 119.3, 122.5, 127.2, 127.8, 128.5, 128.6, 130.3, 136.1, 137.5, 142.7, 149.0, 150.8; MS (ESI): m/z=241.79 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-fdd66b7aaf3340bb9a44b455d3ad4f60
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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