6-Butyl-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione → HCID 19700866, compound

HRID 861972Notes

Reaction equation

HRID 861972 reaction equation
[CH2:1]([N:5]1[C:13](=[O:14])[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15])[CH2:2][CH2:3][CH3:4].[Cl:16][C:17]1[CH:18]=[C:19]([Mg]Br)[CH:20]=[CH:21][CH:22]=1>C1(C)C=CC=CC=1>[OH:15][C:6]1([C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:16])[CH:22]=2)[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:12]2[C:13](=[O:14])[N:5]1[CH2:1][CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 3034656-Butyl-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dioneHCID 178478127HCID 178478127, compound

Product 1

HCID 19700866HCID 19700866, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-65 °C

Procedure

6-(n-Butyl)-pyrrolo[3,4-b]pyridine-5,7-dione (20 g, 98 mmole) was dissolved in toluene (500 mL) and cooled to -65° C. To this mixture was added 3-chlorophenylmagnesium bromide (prepared by heating under reflux 2.5 g magnesium metal, 20 g of 3-chlorobromobenzene and 100 mL of tetrahydrofuran for 1 hour) at such a rate that the temperature of the reaction remain below -40° C. After the addition was complete, the cooling bath was removed and the mixture was allowed to warm to 0° C. The reaction mixture was quenched with aqueous ammonium chloride (25 mL) diluted with ethyl acetate (250 mL) and water (250 mL). After separating the resulting 2 layers, the organic fraction was dried with sodium sulfate (50 g). Filtration, followed by solvent removal gave 7-hydroxy-7-(3-chlorophenyl)-6-(n-butyl)-6,7-dihydropyrrolo[3,4-b]pyridin-5-one as an oil, which was used in the next reaction without further purification.

Workup

  1. customremain below -40° C
  2. additionAfter the addition
  3. customthe cooling bath was removed
  4. temperatureto warm to 0° C
  5. customThe reaction mixture was quenched with aqueous ammonium chloride (25 mL)
  6. additiondiluted with ethyl acetate (250 mL) and water (250 mL)
  7. customAfter separating the resulting 2 layers
  8. dry with materialthe organic fraction was dried with sodium sulfate (50 g)
  9. filtrationFiltration
  10. customfollowed by solvent removal

Sources & evidence

ORD record
ord-f95943067b5a463d934970dd7b5a98fb
Source dataset
uspto-grants-1998_02
Patent number
US05716954

Reaction notes

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