(2-Aminophenyl)boronic acid → HCID 57329789, compound

HRID 1054051Notes

Reaction equation

HRID 1054051 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.[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:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[NH2:1])=[N:21][CH:22]=2)[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

3

Reactant 2

HCID 2773216(2-Aminophenyl)boronic acidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 57329789HCID 57329789, compound

Procedure

Synthesized using 2-aminophenylboronic acid (173 g, 1.26 mmol) and 1a (150 mg, 0.63 mmol) according to Method C. Yellow solid. Yield: 120 mg, 0.48 mmol, 76%. 1H NMR (500 MHz, CDCl3): δH (ppm): 5.17 (s, 2H), 6.74-6.79 (m, 2H), 6.93 (t, J=1.3 Hz, 1H), 7.13 (bs, 1H), 7.16-7.19 (m, 1H), 7.49-7.53 (m, 2H), 7.62 (s, 1H), 7.66 (d, J=8.2 Hz, 1H). 8.48 (d, J=1.8 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.2, 117.3, 117.6, 119.1, 121.1, 122.2, 128.7, 129.3, 130.2, 130.3, 135.8, 137.3, 146.6, 146.7, 159.7; MS (ESI): m/z=250.71 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-35ebb097a9ef4c788c513883e7285598
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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