2-Fluoropyridine-4-boronic acid → HCID 58362625, compound

HRID 2361503Notes

Reaction equation

HRID 2361503 reaction equation
[F:1][C:2]1[CH:7]=[C:6](B(O)O)[CH:5]=[CH:4][N:3]=1.Cl[C:12]1[CH:20]=[CH:19][N:18]2[C:14](=[N:15][C:16]3[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=32)[N:13]=1>>[F:1][C:2]1[CH:7]=[C:6]([C:12]2[CH:20]=[CH:19][N:18]3[C:14](=[N:15][C:16]4[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=43)[N:13]=2)[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 27833962-Fluoropyridine-4-boronic acidHCID 84040321HCID 84040321, compound

Product 1

HCID 58362625HCID 58362625, compound

Procedure

General experimental procedure (A) for Suzuki coupling with 2-fluoropyridin-4-ylboronic acid was followed. Reaction was performed on a 40 mg scale of 2-chloropyrimido[1,2-a]benzimidazole. The residue was purified by HPLC (acetonitrile/water) to give 6.2 mg (12%) of T732 as a white solid. 1H NMR (CD3OD): δ 9.91 (1H, d, J=7.2 Hz), 8.47-8.53 (2H, m, overlapped), 8.39 (PH, d, J=7.2 Hz), 8.25 (1H, m), 8.04 (1H, m), 7.95 (1H, d, J=8.4 Hz), 7.89 (1H, m), 7.76 (1H, m); MS: 265 (M+H+).

Workup

  1. customReaction
  2. customThe residue was purified by HPLC (acetonitrile/water)
  3. customto give 6.2 mg (12%) of T732 as a white solid

Sources & evidence

ORD record
ord-e52e88911b704128972294afd8ef7e29
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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