Dimethylformamide → 4-Chloro-1-hydroxy-6-methyl-2-(1-methyl-1-phenylethyl)-1,2-dihydropyrrolo[3,4-c]pyridine-3-one

HRID 21344Notes

Reaction equation

HRID 21344 reaction equation
[Cl:1][C:2]1[N:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]([CH3:15])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:8])=[O:5].CN([CH:24]=[O:25])C>C1COCC1>[Cl:1][C:2]1[C:3]2[C:4](=[O:5])[N:6]([C:7]([CH3:15])([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:8])[CH:24]([OH:25])[C:16]=2[CH:17]=[C:18]([CH3:20])[N:19]=1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 866283402-chloro-6-methyl-N-(1-methyl-1-phenylethyl)nicotinamide

Product 1

HCID 866283414-Chloro-1-hydroxy-6-methyl-2-(1-methyl-1-phenylethyl)-1,2-dihydropyrrolo[3,4-c]pyridine-3-oneYield 59.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Step 2 of Example 16, 2-chloro-6-methyl-N-(1-methyl-1-phenylethyl)nicotinamide (500 mg, 1.73 mmol) was dissolved in THF (20 mL), and the solution was treated with n-butyllithium-hexane solution (2.71 mol/L, 4.33 mL, 3.23 mmol) and DMF (0.335 mL, 4.33 mmol), followed by purification by flash column chromatography (hexane/ethyl acetate=80/20 to 75/25) to obtain 4-chloro-1-hydroxy-6-methyl-2-(1-methyl-1-phenylethyl)-1,2-dihydropyrrolo[3,4-c]pyridine-3-one (326 mg, yield 59%).

Workup

  1. customfollowed by purification by flash column chromatography (hexane/ethyl acetate=80/20 to 75/25)

Sources & evidence

ORD record
ord-a8e5a174d29a4bef949474274d9ac83f
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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