(1-Benzothiophen-3-yl)boronic acid → HCID 57329787, compound

HRID 1054072Notes

Reaction equation

HRID 1054072 reaction equation
[S:1]1[CH:5]=[C:4](B(O)O)[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[N:13]1([CH2:18][C:19]2[CH:20]=[CH:21][C:22](Br)=[N:23][CH:24]=2)[CH:17]=[CH:16][N:15]=[CH:14]1>>[S:1]1[CH:5]=[C:4]([C:22]2[CH:21]=[CH:20][C:19]([CH2:18][N:13]3[CH:17]=[CH:16][N:15]=[CH:14]3)=[CH:24][N:23]=2)[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2

Participants

3

Reactant 2

HCID 2776344(1-Benzothiophen-3-yl)boronic acidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 57329787HCID 57329787, compound

Procedure

Synthesized using benzo[b]thiophen-3-ylboronic acid (224 mg, 1.26 mmol) and 1a (150 mg, 0.63 mmol) according to Method C. Yellow solid. Yield: 100 mg, 0.34 mmol, 54%. 1H NMR (500 MHz, CDCl3): δH (ppm): 5.27 (s, 2H), 6.99 (t, J=1.3 Hz, 1H), 7.18 (brs, 1H), 7.39-7.42 (m, 1H), 7.43-7.47 (m, 1H), 7.59 (dd, J=8.2, 2.5 Hz, 1H), 7.70 (dd, J=8.2, 0.9 Hz, 1H), 7.82 (s, 1H), 7.90-7.92 (m, 1H), 8.01 (s, 1H), 8.46-8.48 (m, 1H), 8.66-8.67 (m, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=45.5, 119.3, 122.6, 122.8, 124.1, 124.7, 124.8, 127.1, 128.7, 129.4, 135.7, 135.9, 137.0, 137.1, 140.9, 148.6, 155.0; MS (ESI): m/z=292.05 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-aa6864aff0064ec68020c2a4a177df1a
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

Loading…