2-Amino-6-chloropyridine → HCID 45788039, compound

HRID 2382763Notes

Reaction equation

HRID 2382763 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.[O:9]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10]1>>[O:9]1[CH:13]=[CH:12][C:11]([C:4]2[N:3]=[C:2]([NH2:1])[CH:7]=[CH:6][CH:5]=2)=[CH:10]1

Participants

3

Reactant 2

HCID 2062462-Amino-6-chloropyridineHCID 2734358Furan-3-boronic acid

Product 1

HCID 45788039HCID 45788039, compoundYield 54.3%

Procedure

The title compound was prepared following procedure described for intermediate A1 step a), but starting from 2-amino-6-chloropyridine (25.0 g; 194.5 mmol; 1.0 eq.) and furan-3-boronic acid (26.11 g; 233.4 mmol; 1.2 eq.). The crude was purified by flash chromatography (EtOAc/c-Hex, 50:50) to give the title compound as a brown oil (16.91 g; 54%). 1H NMR (DMSO-d6) δ 7.96 (s, 1H), 7.42 (m, 2H), 6.82 (m, 2H), 6.37 (d, J=7.2 Hz, 1H), 4.54 (m, 2H). HPLC, Rt: 1.30 min. (purity 84.9%). LC/MS, M+(ESI): 161.4.

Workup

  1. customThe title compound was prepared following procedure
  2. customThe crude was purified by flash chromatography (EtOAc/c-Hex, 50:50)

Sources & evidence

ORD record
ord-f542c930ebb04ea19c63d0fa50b5b314
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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