Methyl Acrylate → HCID 66663337, compound

HRID 2190192Notes

Reaction equation

HRID 2190192 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].[CH3:7][NH:8][C:9]([C:11]1[C:19]2[C:14](=[N:15][C:16]([N:23]([CH2:28][CH2:29]C=C)[S:24]([CH3:27])(=[O:26])=[O:25])=[C:17]([CH:20]3[CH2:22][CH2:21]3)[CH:18]=2)[O:13][C:12]=1[C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=1)=[O:10]>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(Cl)Cl>[CH3:6][O:5][C:1](=[O:4])[CH:2]=[CH:3][CH2:29][CH2:28][N:23]([C:16]1[N:15]=[C:14]2[O:13][C:12]([C:32]3[CH:33]=[CH:34][C:35]([CH3:38])=[CH:36][CH:37]=3)=[C:11]([C:9](=[O:10])[NH:8][CH3:7])[C:19]2=[CH:18][C:17]=1[CH:20]1[CH2:22][CH2:21]1)[S:24]([CH3:27])(=[O:26])=[O:25]

Participants

5

Reactant 2

HCID 7294Methyl AcrylateHCID 58052428HCID 58052428, compound

Product 1

HCID 66663337HCID 66663337, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 178425456HCID 178425456, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Grubbs II catalyst (4.7 mg, 0.005 mmol, 0.05 equiv) in DCM (1.0 mL) was added methyl acrylate (95 mg, 1.1 mmol, 10 equiv) followed by a solution of 6-(But-3-enyl-methanesulfonyl-amino)-5-cyclopropyl-2-p-tolyl-furo[2,3-b]pyridine-3-carboxylic acid methylamide (50 mg, 0.11 mmol, 1.0 equiv) in DCM (1.0 mL). The solution was stirred at room temperature for 2 hours, after which the solvent was removed under vacuum. The residue was purified by silica gel column chromatography, EtOAc/heptane 70% to give product 35 mg. MS (ESI) m/z 512.6 (M+1). Retention time=1.50 min, Method LC-C8 broad range-NpH.

Workup

  1. customafter which the solvent was removed under vacuum
  2. customThe residue was purified by silica gel column chromatography, EtOAc/heptane 70%

Sources & evidence

ORD record
ord-641ea531ccf7416b8fc586adb5b9ed47
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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