2-Thiopheneboronic acid → HCID 57329792, compound

HRID 1054066Notes

Reaction equation

HRID 1054066 reaction equation
[S: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>>[N:9]1([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[N:19][CH:20]=2)[CH:13]=[CH:12][N:11]=[CH:10]1

Participants

3

Reactant 2

HCID 27339602-Thiopheneboronic acidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 57329792HCID 57329792, compound

Procedure

Synthesized using 2-thiophenylboronic acid (118 g, 0.92 mmol) and 1a (110 mg, 0.46 mmol) according to Method C. Yellow solid. Yield: 101 mg, 0.42 mmol, 91%. 1H NMR (CDCl3, 500 MHz): δH (ppm): 5.13 (s, 2H), 6.90 (s, 1H), 7.11 (t, J=4.4 Hz, 2H), 7.41-7.43 (m, 2H), 7.57-7.59 (m, 2H), 7.63 (d, J=8.2 Hz, 1H), 8.45 (d, J=1.9 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.1, 118.9, 119.0, 125.1, 128.13, 128.14, 129.8, 130.3, 135.7, 137.3, 144.0, 148.4, 152.9; MS (ESI): m/z=242.10 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-399fcbe91c894e69a01e4f7e8c9b3f4f
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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