3-Cyanophenylboronic acid → HCID 67515874, compound

HRID 1054055Notes

Reaction equation

HRID 1054055 reaction equation
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)#[N:2].[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:7]3[CH:8]=[C:3]([CH:4]=[CH:5][CH:6]=3)[C:1]#[N:2])=[N:22][CH:23]=2)[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

3

Reactant 2

HCID 27343253-Cyanophenylboronic acidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 67515874HCID 67515874, compound

Procedure

Synthesized using 3-cyanophenylboronic acid (185 mg, 1.26 mmol) and 1a (150 mg, 0.63 mmol) according to Method C. Yellow solid. Yield: 135 mg, 0.52 mmol, 82%. 1H NMR (CDCl3, 500 MHz): δH (ppm): 5.21 (s, 2H), 6.94 (s, 1H), 7.13 (s, 1H), 7.54 (dd, J=8.2, 2.4 Hz, 1H), 7.55-7.60 (m, 2H), 7.70 (d, J=7.9 Hz, 1H), 7.73 (d, J=8.2 Hz, 1H), 8.21 (d, J=7.9 Hz, 1H), 8.31 (s, 1H), 8.61 (d, J=1.5 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.0, 113.1, 118.6, 119.0, 120.6, 129.7, 130.4, 130.6, 131.0, 131.3, 132.5, 136.0, 137.3, 139.6, 148.77, 148.81, 155.1; MS (ESI): m/z=261.41 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-907735d99ba74d2e8b9ed1bb5c78ae53
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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