2-Fluorophenylboronic acid → HCID 57329788, compound

HRID 1054043Notes

Reaction equation

HRID 1054043 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.[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:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:20]1[CH:19]=[CH:18][C:17]([CH2:16][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:22][N:21]=1

Participants

3

Reactant 2

HCID 27343542-Fluorophenylboronic acidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 57329788HCID 57329788, compound

Procedure

Synthesized using 2-fluorophenylboronic acid (176 mg, 1.26 mmol) and 1a (150 mg, 0.63 mmol) according to Method C. Yellow solid. Yield: 112 mg, 0.44 mmol, 70%. 1H NMR (500 MHz, CDCl3): δH (ppm): 5.18 (s, 2H), 6.93 (t, J=1.3 Hz, 1H), 7.12 (bs, 1H), 7.15 (ddd, J=11.7, 8.2, 1.3 Hz, 1H), 7.26 (dt, J=7.9, 1.3 Hz, 1H), 7.36-7.40 (m, 1H), 7.48 (dd, J=8.2, 2.5 Hz, 1H), 7.59 (s, 1H), 7.78 (ddd, J=8.2, 2.2, 0.9 Hz, 1H), 7.97 (dt, J=7.9, 1.9 Hz, 1H), 8.60 (dd, J=2.5, 0.6 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.1, 116.2 (d, J=23.0 Hz), 119.0, 124.5 (d, J=9.1 Hz), 124.6, 126.6, 126.7, 130.0 (d, J=9.1 Hz), 130.7 (d, J=9.1 Hz), 130.9 (d, J=2.7 Hz), 135.3, 137.3, 148.5, 153.6 (d, J=2.7 Hz), 160.4 (d, J=250.2 Hz); MS (ESI): m/z=254.18 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-dd72a705cdc24676b615a9a5e0d00b9e
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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