Triethylamine → HCID 58437100, compound

HRID 1942327Notes

Reaction equation

HRID 1942327 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[P:9]([O-])([O:14][CH2:15][CH3:16])([O:11][CH2:12][CH3:13])=[O:10].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([P:9](=[O:10])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 706222-Amino-5-bromopyridineHCID 5166299Diethyl phosphoric acid

Product 1

HCID 58437100HCID 58437100, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-amino-5-bromopyridine (5 g, 0.029 mol; Aldrich Chemical Company, Inc., Milwaukee, Wis.), diethyl phosphate (5.02 g, 0.036 mol), triethylamine (4.4 g, 0.043 mol), Pd(OAc)2 (0.78 g, 3.4 mmol), triphenylphosphine (2.28 g, 8.7 mmol) in ethanol (100 mL) was refluxed for 14 hours under nitrogen. TLC (Petroleum ether/ethyl acetate=1:1) indicated that the reaction was complete. The resulting mixture was filtered, and the filtrate was concentrated in vacuo, the residue was purified by prep. HPLC to afford (I-25a) (4.3 g, 64.4%) as a white solid; m/z 231.3 (M+H)+.

Workup

  1. temperaturewas refluxed for 14 hours under nitrogen
  2. filtrationThe resulting mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customthe residue was purified by prep
  5. customHPLC to afford (I-25a) (4.3 g, 64.4%) as a white solid

Sources & evidence

ORD record
ord-c391d4fcee1a45f0ba3033d3fcc0cf2d
Source dataset
uspto-grants-2013_03
Patent number
US08389552B2

Reaction notes

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