Benzo[b]furan-2-boronic acid → HCID 70691516, compound

HRID 1054075Notes

Reaction equation

HRID 1054075 reaction equation
[O: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>>[O: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 2776266Benzo[b]furan-2-boronic acidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 70691516HCID 70691516, compound

Procedure

Synthesized using benzo[b]furan-2-ylboronic acid (204 mg, 1.26 mmol) and 1a (150 mg, 0.63 mmol) according to Method C. Yellow solid. Yield: 71 mg, 0.26 mmol, 41%. 1H NMR (CDCl3, 500 MHz): δH (ppm): 5.18 (s, 2H), 6.93 (s, 1H), 7.13 (s, 1H), 7.25-7.28 (m, 2H), 7.35 (dt, J=8.2, 1.2 Hz, 1H), 7.44 (d, J=0.9 Hz, 1H), 7.51 (dd, J=8.2, 2.1 Hz, 1H), 7.56 (dd, J=8.2, 0.9 Hz, 1H), 7.60 (s, 1H), 7.65 (d, J=7.3 Hz, 1H), 7.88 (d, J=8.2 Hz, 1H), 8.56 (d, J=2.1 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.1, 105.5, 111.5, 119.0, 119.8, 121.8, 123.3, 125.5, 128.6, 130.4, 130.8, 135.7, 137.3, 148.7, 149.4, 154.3, 155.4; MS (ESI): m/z=276.03 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-e55ade8115424f6280380f1afdd0537a
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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