5-Formyl-2-thiopheneboronic acid → HCID 57329791, compound

HRID 1054069Notes

Reaction equation

HRID 1054069 reaction equation
[CH:1]([C:3]1[S:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[O:2].[N:11]1([CH2:16][C:17]2[CH:18]=[CH:19][C:20](Br)=[N:21][CH:22]=2)[CH:15]=[CH:14][N:13]=[CH:12]1>>[N:11]1([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C:6]3[S:7][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=3)=[N:21][CH:22]=2)[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

3

Reactant 2

HCID 27734305-Formyl-2-thiopheneboronic acidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 57329791HCID 57329791, compound

Procedure

Synthesized using 5-formyl-2-thiophenylboronic acid (197 mg, 1.26 mmol) and 1a (150 mg, 0.63 mmol) according to Method C. Yellow solid. Yield: 78 mg, 0.28 mmol, 46%. 1H NMR (500 MHz, CDCl3): δH (ppm): 5.18 (s, 2H), 6.92 (t, J=1.3 Hz, 1H), 7.13 (t, J=1.3 Hz, 1H), 7.47 (dd, J=8.2, 2.2 Hz, 1H), 7.56 (brs, 1H), 7.66 (d, J=4.1 Hz, 1H), 7.71 (dd, J=8.2, 0.6 Hz, 1H), 7.76 (d, J=4.1 Hz, 1H), 8.52 (dd, J=2.2, 0.6 Hz, 1H), 9.93 (s, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.0, 119.0, 119.8, 125.5, 130.5, 131.7, 135.8, 136.7, 137.3, 144.6, 148.7, 151.4, 152.8, 183.0; MS (ESI): m/z=270.22 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-288126e58f55474ba61f39288ebe2836
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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