Benzo(B)Thiophene-2-Boronic Acid → HCID 70685192, compound

HRID 1054071Notes

Reaction equation

HRID 1054071 reaction equation
[S:1]1[C:5](B(O)O)=[CH:4][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[C:5]([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)=[CH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2

Participants

3

Reactant 2

HCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 70685192HCID 70685192, compound

Procedure

Synthesized using benzo[b]thiophen-2-ylboronic acid (149 mg, 0.84 mmol) and 1a (100 mg, 0.42 mmol) according to Method C. Yellow solid. Yield: 46 mg, 0.16 mmol, 38%. 1H NMR (CDCl3, 500 MHz): δH (ppm): 5.17 (s, 2H), 6.93 (t, J=1.3 Hz, 1H), 7.35-7.38 (m, 2H), 7.46 (dd, J=8.2, 2.2 Hz, 1H), 7.60 (brs, 1H), 7.79 (d, J=8.2 Hz, 1H), 7.80-7.83 (m 1H), 7.84 (d, J=0.6 Hz, 1H), 7.86-7.88 (m, 1H), 8.52 (d, J=1.9 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.1, 119.0, 119.7, 121.7, 122.6, 124.2, 123.6, 125.3, 130.4, 130.6, 135.6, 137.3, 140.3, 140.8, 143.8, 148.5, 152.8; MS (ESI): m/z=292.04 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-fe3c8a1251234e33868829e4efa90b74
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

Loading…