Thiophene-3-boronic acid → HCID 67515607, compound

HRID 1054067Notes

Reaction equation

HRID 1054067 reaction equation
[S: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>>[N:9]1([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:3]3[CH:4]=[CH:5][S:1][CH:2]=3)=[N:19][CH:20]=2)[CH:13]=[CH:12][N:11]=[CH:10]1

Participants

3

Reactant 2

HCID 581760Thiophene-3-boronic acidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 67515607HCID 67515607, compound

Procedure

Synthesized using 3-thiophenylboronic acid (206 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): δH (ppm): 5.15 (s, 2H), 6.91 (t, J=1.3 Hz, 1H), 7.12 (s, 1H), 7.40 (dd, J=5.0, 3.2 Hz, 1H), 7.45 (dd, J=8.2, 2.2 Hz, 1H), 7.58 (s, 1H), 7.60 (dd, J=8.2, 0.6 Hz, 1H), 7.64 (dd, J=5.0, 1.3 Hz, 1H), 7.91 (dd, J=3.2, 1.3 Hz, 1H), 8.51 (dd, J=2.2, 0.6 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.1, 119.0, 120.3, 124.4, 126.1, 126.5, 129.6, 130.3, 135.7, 137.3, 141.4, 148.6, 153.8; MS (ESI): m/z=242.03 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-9548fdea4a8d498c823b9ab83170fb58
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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