Triphenylphosphine → (R)-4-((R)-1-(6-(3,4-dimethoxyphenyl)-3-methyl-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)pyrrolidin-2-one

HRID 2209056Notes

Reaction equation

HRID 2209056 reaction equation
[OH:1][C@H:2]([C@H:4]1[CH2:8][NH:7][C:6](=[O:9])[CH2:5]1)[CH3:3].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([C:39]2[N:44]=[C:43](O)[C:42]3[N:46]([CH3:49])[CH:47]=[N:48][C:41]=3[CH:40]=2)[CH:34]=[CH:35][C:36]=1[O:37][CH3:38].CCOC(/N=N/C(OCC)=O)=O>C(Cl)Cl.CCOC(C)=O.O>[CH3:29][O:30][C:31]1[CH:32]=[C:33]([C:39]2[N:44]=[C:43]([O:1][C@@H:2]([C@H:4]3[CH2:8][NH:7][C:6](=[O:9])[CH2:5]3)[CH3:3])[C:42]3[N:46]([CH3:49])[CH:47]=[N:48][C:41]=3[CH:40]=2)[CH:34]=[CH:35][C:36]=1[O:37][CH3:38]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 66713239(R)-4-((S)-1-hydroxyethyl)pyrrolidin-2-oneHCID 178488439HCID 178488439, compound

Product 1

HCID 117842943(R)-4-((R)-1-(6-(3,4-dimethoxyphenyl)-3-methyl-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)pyrrolidin-2-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of (R)-4-((R)-1-hydroxyethyl)pyrrolidin-2-one 1.18 (350 mg, 2.73 mmol), PPh3 (720 mg, 2.73 mmol), and 6-(3,4-dimethoxyphenyl)-3-methyl-3H-imidazo[4,5-c]pyridin-4-ol 2.27 (130 mg, 0.60 mmol) in CH2Cl2 (6 mL) was added DEAD (475 mg, 2.73 mmol) and the reaction was stirred overnight. Water (10 mL) and EtOAc (20 mL) were added and the layers were separated. The organic layer was washed with brine (1×10 mL), dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (CH2Cl2→10% MeOH in CH2Cl2) to afford (R)-4-((R)-1-(6-(3,4-dimethoxyphenyl)-3-methyl-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)pyrrolidin-2-one 3.01.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with brine (1×10 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (CH2Cl2→10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-9be0bad448694c45843fd69a44c20c25
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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