(3-Amino-4-methylphenyl)boronic acid → HCID 67516475, compound

HRID 1054054Notes

Reaction equation

HRID 1054054 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][C:7]=1[CH3:8].[N:12]1([CH2:17][C:18]2[CH:19]=[CH:20][C:21](Br)=[N:22][CH:23]=2)[CH:16]=[CH:15][N:14]=[CH:13]1>>[N:12]1([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:4]3[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([NH2:1])[CH:3]=3)=[N:22][CH:23]=2)[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

3

Reactant 2

HCID 2737803(3-Amino-4-methylphenyl)boronic acidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 67516475HCID 67516475, compound

Procedure

Synthesized using 3-amino-4-methylphenylboronic acid (190 mg, 1.26 mmol) and 1a (150 mg, 0.63 mmol) according to Method C. Yellow solid. Yield: 139 mg, 0.52 mmol, 84%. 1H NMR (500 MHz, CDCl3): δH (ppm): 2.22 (s, 3H), 5.16 (s, 2H), 6.92 (t, J=0.9 Hz, 1H), 7.12 (t, J=0.9 Hz, 1H), 7.13 (d, J=7.9 Hz, 1H), 7.26 (dd, J=7.9, 1.9 Hz, 1H), 7.37 (d, J=1.9 Hz, 1H), 7.45 (dd, J=8.2, 2.2 Hz, 1H), 7.59 (s, 1H), 7.67 (dd, J=8.2, 0.6 Hz, 1H), 8.55 (dd, J=2.2, 0.6 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=17.2, 48.2, 113.2, 117.1, 119.0, 120.4, 123.9, 129.6, 130.2, 130.9, 135.6, 137.3, 137.4, 145.1, 148.4, 157.8; MS (ESI): m/z=264.25 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-f50772ffbcf44213b7078a97db9dc320
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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