3-Aminophenylboronic acid → HCID 44456104, compound

HRID 1054052Notes

Reaction equation

HRID 1054052 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.[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:4]3[CH:3]=[C:2]([NH2:1])[CH:7]=[CH:6][CH:5]=3)=[N:21][CH:22]=2)[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

3

Reactant 2

HCID 922693-Aminophenylboronic acidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 44456104HCID 44456104, compound

Procedure

Synthesized using 3-aminophenylboronic acid 230 mg, 1.68 mmol) and 1a (200 mg, 0.84 mmol) according to Method C. Orange solid. Yield: 144 mg, 0.56 mmol, 67%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=5.11 (s, 2H), 6.72 (ddd, J=7.6, 2.4, 0.9 Hz, 1H), 6.89 (brs, 1H), 7.08 (bs, 1H), 7.21 (t, J=7.7 Hz, 1H), 7.28 (dt, J=7.8, 1.3 Hz, 1H), 7.33 (t, J=2.2 Hz, 1H), 7.41 (dd, J=8.2, 2.2 Hz, 1H), 7.55 (brs, 1H), 7.62 (d, J=8.2 Hz, 1H), 8.50 (d, J=2.2 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.0, 113.3, 116.0, 117.0, 119.0, 120.5, 129.6, 129.9, 130.1, 135.6, 137.2, 139.5, 146.9, 148.3, 157.6; MS (ESI): m/z=251.13 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-c5709838d17d400c8a4a3904a9cf8fbd
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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