3-Fluorophenylboronic acid → 2-(3-Fluoro-phenyl)-5-imidazol-1-ylmethyl-pyridine

HRID 1054044Notes

Reaction equation

HRID 1054044 reaction equation
[F: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>>[F:1][C:2]1[CH:3]=[C:4]([C:20]2[CH:19]=[CH:18][C:17]([CH2:16][N:11]3[CH:15]=[CH:14][N:13]=[CH:12]3)=[CH:22][N:21]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 27339863-Fluorophenylboronic acidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 675104312-(3-Fluoro-phenyl)-5-imidazol-1-ylmethyl-pyridine

Procedure

Synthesized using 3-fluorophenylboronic acid (230 mg, 1.68 mmol) and 1a (200 mg, 0.84 mmol) according to Method C. Yellow solid. Yield: 135 mg, 0.53 mmol, 64%. 1H NMR (CDCl3, 500 MHz): δH (ppm): 5.19 (s, 2H), 6.93 (s, 1H), 7.11 (ddd, J=8.2, 2.5, 0.9 Hz, 1H), 7.13 (dd, J=2.5, 0.9 Hz, 1H), 7.43 (ddd, J=8.2, 7.9, 6.0 Hz, 1H), 7.50 (dd, J=8.2, 2.5 Hz, 1H), 7.59 (brs, 1H), 7.69-7.76 (m, 3H), 8.58 (dd, J=2.2, 0.6 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.0, 113.9 (d, J=23.0 Hz), 116.1 (d, J=21.1 Hz), 119.0, 120.6, 122.4 (d, J=2.9 Hz), 130.3 (d, J=7.6 Hz), 130.4, 130.7, 135.8, 137.3, 140.8 (d, J=7.6 Hz), 148.6, 156.3 (d, J=2.9 Hz), 163.5 (d, J=245.7 Hz); MS (ESI): m/z=254.13 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-9daa6e35a75b4c679463ee8f0d9c2076
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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