3,4-Dimethoxyphenylboronic acid → HCID 44456068, compound

HRID 1054050Notes

Reaction equation

HRID 1054050 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[N:14]1([CH2:19][C:20]2[CH:21]=[CH:22][C:23](Br)=[N:24][CH:25]=2)[CH:18]=[CH:17][N:16]=[CH:15]1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:23]2[CH:22]=[CH:21][C:20]([CH2:19][N:14]3[CH:18]=[CH:17][N:16]=[CH:15]3)=[CH:25][N:24]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

3

Reactant 2

HCID 27347023,4-Dimethoxyphenylboronic acidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 44456068HCID 44456068, compound

Procedure

Synthesized using 3,4-dimethoxyphenylboronic acid (610 mg, 3.36 mmol) and 1a (400 mg, 1.68 mmol) according to Method C. Yellow solid. Yield: 470 mg, 1.58 mmol, 94%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=3.93 (s, 3H), 3.98 (s, 3H), 5.16 (s, 2H), 6.92 (br, s, 1H), 6.94 (d, J=8.5 Hz, 1H), 7.11 (bs, 1H), 7.46 (dd, J=8.5, 2.2 Hz, 1H), 7.47 (dd, J=8.5, 2.2 Hz, 1H), 7.58 (bs, 1H), 7.65 (d, J=2.2 Hz, 1H), 7.67 (d, J=8.5 Hz, 1H), 8.54 (d, J=2.2 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.1, 56.0, 56.0, 113.3, 110.0, 111.1, 119.0, 119.5, 120.0, 129.4, 130.3, 131.4, 135.7, 148.4, 149.4, 150.3, 157.3; MS (ESI): m/z=296.17 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-641d5f0a2b1449bcbde5593af2bf8c2d
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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