Triethylamine → HCID 11405713, compound

HRID 1272095Notes

Reaction equation

HRID 1272095 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([O:23][CH3:24])=[C:13]([C:15]2[CH:20]=[C:19]([NH2:21])[N:18]=[C:17]([NH2:22])[CH:16]=2)[CH:14]=1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([O:23][CH3:24])=[C:13]([C:15]2[CH:16]=[C:17]([NH2:22])[N:18]=[C:19]([NH:21][C:29]3[CH:30]=[CH:31][C:26]([Cl:25])=[CH:27][CH:28]=3)[CH:20]=2)[CH:14]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 742994-Chlorophenylboronic acidHCID 69422628HCID 69422628, compound

Product 1

HCID 11405713HCID 11405713, compoundYield 33.3%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-(5-chloro-2-methoxy-phenyl)-pyridine-2,6-diamine trifluoroacetic acid salt (90 mg, 0.25 mmol), 4-chloro-phenylboronic acid (45 mg, 0.29 mmol), copper (II) acetate (218 mg, 1.2 mmol), 4A molecular sieves (5 g) in dichloromethane (20 ml) was added triethylamine (0.3 ml). The mixture was stirred under an oxygen atmosphere for 40 minutes and filtered through a pad of celite under suction. After evaporation of volatiles under reduced pressure, the residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (3:5 followed by 1:1 followed by 5:3) to provide the title compound (30 mg, 33% yield). 1H NMR (acetone-d6) δ 3.84 (s, 3H, CH3), 5.33 (d, 2H, J=8.8 Hz, NH2), 6.16 (d, 1H, J=1.1 Hz, Ar), 6.27 (t, 1H, J=1.1 Hz, Ar), 7.12 (d, 1H, J=8.8 Hz, Ar), 7.23 (d, 2H, J=8.9 Hz, Ar), 7.30 (d, 1H, J=2.7 Hz, Ar), 7.36 (dd, 1H, J=8.8 Hz, J=2.7 Hz, Ar), 7.76–7.79 (m, 2H, Ar), 8.05 (s, 1H, NH).

Workup

  1. filtrationfiltered through a pad of celite under suction
  2. customAfter evaporation of volatiles under reduced pressure
  3. customthe residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (3:5 followed by 1:1 followed by 5:3)

Sources & evidence

ORD record
ord-896894a38369479b97e933e1bd040105
Source dataset
uspto-grants-2007_04
Patent number
US07208507B2

Reaction notes

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