Triethylamine → HCID 54721906, compound

HRID 2109861Notes

Reaction equation

HRID 2109861 reaction equation
[OH:1][C:2]1[C:3]([OH:22])=[C:4]2[C:9](=[O:10])[N:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14](I)[CH:13]=3)[CH2:7][CH2:6][N:5]2[C:19](=[O:21])[CH:20]=1.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>CN(C=O)C.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[C:14]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:15]=[CH:16][CH:17]=[C:12]([CH2:11][N:8]2[CH2:7][CH2:6][N:5]3[C:19](=[O:21])[CH:20]=[C:2]([OH:1])[C:3]([OH:22])=[C:4]3[C:9]2=[O:10])[CH:13]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 57634648HCID 57634648, compound

Product 1

HCID 54721906HCID 54721906, compound

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 8,9-dihydroxy-2-(3-iodobenzyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,6-dione (0.05 g, 0.121 mmol) in DMF (5 mL) was degassed for 5 minutes with nitrogen and placed under an atmosphere of nitrogen. To this was added phenyl boronic acid (0.015 g, 0.123 mmol), triethylamine (0.051 mL, 0.364 mmol), and bis(tri-t-butylphosphine)palladium(0) (0.003 g, 0,006 mmol) and heated with stirring at 110° C. overnight. The product mixture was concentrated under vacuum, and the residue was triturated with methylene chloride. The resultant precipitate was filtered off and the filtrate concentrated under vacuum. The filtrate residue was subjected to HPLC purification on C-18 stationary phase eluted with water/acetonitrile/TFA mobile phase. Desired fractions were concentrated under vacuum to afford the title compound as off white solid.

Workup

  1. temperatureheated
  2. concentrationThe product mixture was concentrated under vacuum
  3. customthe residue was triturated with methylene chloride
  4. filtrationThe resultant precipitate was filtered off
  5. concentrationthe filtrate concentrated under vacuum
  6. customThe filtrate residue was subjected to HPLC purification on C-18 stationary phase
  7. washeluted with water/acetonitrile/TFA mobile phase
  8. concentrationDesired fractions were concentrated under vacuum

Sources & evidence

ORD record
ord-7c4e5e086b864dc7ae310a528420cf4b
Source dataset
uspto-grants-2009_04
Patent number
US07517532B2

Reaction notes

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