Methyl 3-butenoate → (E)-Methyl 7-(2,3-diphenyl-7,8-dihydropyrido[3,2-b]pyrazin-5(6H)-yl)hept-3-enoate

HRID 406209

Reaction equation

HRID 406209 reaction equation
[CH2:1]([N:6]1[C:15]2[C:10](=[N:11][C:12]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:14]=2)[CH2:9][CH2:8][CH2:7]1)[CH2:2][CH2:3][CH:4]=[CH2:5].[C:28]([O:33][CH3:34])(=[O:32])[CH2:29]C=C>C(Cl)Cl.Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1>[C:22]1([C:12]2[N:11]=[C:10]3[CH2:9][CH2:8][CH2:7][N:6]([CH2:1][CH2:2][CH2:3]/[CH:4]=[CH:5]/[CH2:29][C:28]([O:33][CH3:34])=[O:32])[C:15]3=[N:14][C:13]=2[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 77314Methyl 3-butenoateHCID 666663485-(Pent-4-enyl)-2,3-diphenyl-5,6,7,8-tetrahydropyrido[3,2-b]pyrazine

Product 1

HCID 66665849(E)-Methyl 7-(2,3-diphenyl-7,8-dihydropyrido[3,2-b]pyrazin-5(6H)-yl)hept-3-enoate

Reagents, catalysts & solvents 2

HCID 178425456HCID 178425456, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(pent-4-enyl)-2,3-diphenyl-5,6,7,8-tetrahydropyrido[3,2-b]pyrazine (step 1) (200 mg, 0.563 mmol) and methyl but-3-enoate (225 mg, 2.251 mmol) in DCM (300 ml) was added Grubbs Catalyst second generation (5 mol %, 23.88 mg, 0.028 mmol). The reaction was stirred at RT under an atmosphere of nitrogen overnight. An additional portion of Grubbs Catalyst second generation (5 mol %, 23.88 mg, 0.028 mmol) was added and stirring continued for 2.5 h. The solvent was removed in vacuo and the resulting crude was purified by chromatography on silica eluting with EtOAc/iso-hexane to afford the title compound;

Workup

  1. stirringstirring
  2. waitcontinued for 2.5 h
  3. customThe solvent was removed in vacuo
  4. customthe resulting crude was purified by chromatography on silica eluting with EtOAc/iso-hexane

Sources & evidence

ORD record
ord-cb671b216bce4c3a9ff3acd542238359
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Linked notes

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