Phenylboronic Acid → 5-Imidazol-1-ylmethyl-2,3-diphenyl-pyridine

HRID 1054061Notes

Reaction equation

HRID 1054061 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[C:12](Cl)=[N:13][CH:14]=[C:15]([CH2:17][N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)[CH:16]=1>>[N:18]1([CH2:17][C:15]2[CH:16]=[C:11]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:12]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[N:13][CH:14]=2)[CH:22]=[CH:21][N:20]=[CH:19]1

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 706831103-Bromo-2-chloro-5-imidazol-1-ylmethyl-pyridine

Product 1

HCID 675158695-Imidazol-1-ylmethyl-2,3-diphenyl-pyridine

Procedure

Synthesized using phenylboronic acid (134 mg, 1.10 mmol) and 6 (150 mg, 0.55 mmol) according to Method C. Yellow solid. Yield: 79 mg, 0.25 mmol, 46%. 1H NMR (500 MHz, CDCl3): δH (ppm): 5.27 (s, 2H), 7.00 (brs, 1H), 7.11-7.13 (m, 2H), 7.16 (brs, 1H), 7.21-7.28 (m, 6H), 7.32-7.34 (m, 2H), 7.49 (d, J=2.1 Hz, 1H), 8.60 (d, J=2.1 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.3, 119.2, 127.6, 128.0, 128.1, 128.4, 129.2, 129.4, 129.8, 136.4, 137.1, 137.5, 139.0, 139.3, 147.1, 147.1, 157.6; MS (ESI): m/z=312.10 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-495318ca6770442698da5d21a643a6e7
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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