(3-Fluoro-4-hydroxyphenyl)boronic acid → 2-Fluoro-4-(5-imidazol-1-ylmethyl-pyridin-2-yl)-phenol

HRID 1054047Notes

Reaction equation

HRID 1054047 reaction equation
[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][C:7]=1[OH:8].[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>>[F:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:20]=[CH:19][C:18]([CH2:17][N:12]3[CH:16]=[CH:15][N:14]=[CH:13]3)=[CH:23][N:22]=2)[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

3

Reactant 2

HCID 23005361(3-Fluoro-4-hydroxyphenyl)boronic acidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 1360081152-Fluoro-4-(5-imidazol-1-ylmethyl-pyridin-2-yl)-phenol

Procedure

Synthesized using 3-fluoro-4-hydroxyphenylboronic acid (196 mg, 2.00 mmol) and 1a (150 mg, 0.63 mmol) according to Method C. Yellow solid. Yield: 40 mg, 0.15 mmol, 24%. 1H NMR (500 MHz, DMSO-d6): δH (ppm): 5.25 (s, 2H), 6.92 (brs, 1H), 7.03 (t, J=8.8 Hz, 1H), 7.25 (t, J=1.2 Hz, 1H), 7.69 (dd, J=8.2, 2.2 Hz, 1H), 7.74 (ddd, J=8.5, 2.2, 0.6 Hz, 1H), 7.80 (brs, 1H), 7.83 (dd, J=13.0 Hz, 2.2 Hz, 1H), 7.87 (dd, J=8.2, 0.6 Hz, 1H), 8.57 (dd, J=2.2, 0.6 Hz, 1H), 10.2 (s, 1H); MS (ESI): m/z=270.12 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-c5dc0e112a4a4e1ea52105b34caabe0a
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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