Potassium Carbonate → Ethyl 7-(3-chloro-2-(pyridin-4-yl)-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

HRID 2276571Notes

Reaction equation

HRID 2276571 reaction equation
Br[C:2]1[N:3]=[C:4]2[CH2:12][CH2:11][CH2:10][N:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:5]2=[N:6][C:7]=1[Cl:8].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:8][C:7]1[N:6]=[C:5]2[N:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:10][CH2:11][CH2:12][C:4]2=[N:3][C:2]=1[C:12]1[CH:11]=[CH:10][N:9]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86681854Ethyl 7-(2-bromo-3-chloro-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

Product 1

HCID 86681855Ethyl 7-(3-chloro-2-(pyridin-4-yl)-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of ethyl 7-(2-bromo-3-chloro-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate (step 2) (100 mg, 0.247 mmol) and potassium carbonate (102 mg, 0.741 mmol) in dioxane (2 ml) was degassed by bubbling nitrogen through (×3). Pd(Ph3P)4 (28.6 mg, 0.025 mmol) was added and the mixture was degassed by bubbling nitrogen through (×3). The mixture was heated at 150° C. for 2 hours using microwave irradiation. The mixture was diluted with water and extracted with EtOAc (×2). The organics were washed with brine, dried (MgSO4) and evaporated under vacuum to a pale oil. The crude was purified by chromatography on silica eluting with 20-100% EtOAc/iso-hexane to give the title compound as a clear oil;

Workup

  1. customwas degassed
  2. customby bubbling nitrogen through (×3)
  3. customthe mixture was degassed
  4. customby bubbling nitrogen through (×3)
  5. custommicrowave irradiation
  6. additionThe mixture was diluted with water
  7. extractionextracted with EtOAc (×2)
  8. washThe organics were washed with brine
  9. dry with materialdried (MgSO4)
  10. customevaporated under vacuum to a pale oil
  11. customThe crude was purified by chromatography on silica eluting with 20-100% EtOAc/iso-hexane

Sources & evidence

ORD record
ord-518121ec41f9419a99b9fe634bac1355
Source dataset
uspto-grants-2015_09
Patent number
US09132127B2

Reaction notes

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