(Pyrimidin-5-yl)boronic acid → HCID 67516179, compound

HRID 1054064Notes

Reaction equation

HRID 1054064 reaction equation
[N:1]1[CH:6]=[C:5](B(O)O)[CH:4]=[N:3][CH:2]=1.[N:10]1([CH2:15][C:16]2[CH:17]=[CH:18][C:19](Br)=[N:20][CH:21]=2)[CH:14]=[CH:13][N:12]=[CH:11]1>>[N:10]1([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:5]3[CH:6]=[N:1][CH:2]=[N:3][CH:4]=3)=[N:20][CH:21]=2)[CH:14]=[CH:13][N:12]=[CH:11]1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 67516179HCID 67516179, compound

Procedure

Synthesized using pyrimid-5-ylboronic acid (155 mg, 1.26 mmol) and 1a (150 mg, 0.63 mmol) according to Method C. Yellow solid. Yield: 121 mg, 0.51 mmol, 81%. 1H NMR (500 MHz, CDCl3): δH (ppm): 5.23 (s, 2H), 6.93 (t, J=1.3 Hz, 1H), 7.12 (t, J=1.3 Hz, 1H), 7.57 (dd, J=8.2, 2.5 Hz, 1H), 7.67 (s, 1H), 7.74 (dd, J=8.2, 0.9 Hz, 1H), 8.62 (m, 1H), 9.23 (s, 1H), 9.29 (s, 2H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.0, 119.0, 120.5, 130.1, 131.6, 131.8, 136.1, 137.3, 149.2, 152.1, 155.0, 158.8; MS (ESI): m/z=238.10 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-03d7af7672204dc987f8c7082384256d
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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