Water → 5-Methyl-2-[2-(1-methyl-1H-benzoimidazol-2-yl)-ethyl]-7-pyridin-3-yl-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dione

HRID 1752626Notes

Reaction equation

HRID 1752626 reaction equation
C([O-])([O-])=O.[K+].[K+].Cl[C:8]1[C:13](=[O:14])[N:12]([CH3:15])[CH:11]=[C:10]2[CH2:16][N:17]([CH2:20][CH2:21][C:22]3[N:26]([CH3:27])[C:25]4[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=4[N:23]=3)[C:18](=[O:19])[C:9]=12.[N:32]1[CH:37]=[CH:36][CH:35]=[C:34](B(O)O)[CH:33]=1.O>CN(C=O)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)Cl>[CH3:15][N:12]1[C:13](=[O:14])[C:8]([C:34]2[CH:33]=[N:32][CH:37]=[CH:36][CH:35]=2)=[C:9]2[C:18](=[O:19])[N:17]([CH2:20][CH2:21][C:22]3[N:26]([CH3:27])[C:25]4[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=4[N:23]=3)[CH2:16][C:10]2=[CH:11]1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 717435967-Chloro-5-methyl-2-(2-(1-methyl-1H-benzo[D]imidazol-2-YL)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-C]pyridine-1,6(5H)-dione

Product 1

HCID 862962735-Methyl-2-[2-(1-methyl-1H-benzoimidazol-2-yl)-ethyl]-7-pyridin-3-yl-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dioneYield 22.33%

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

K2CO3 (232 mg, 1.682 mmol) and bis(triphenylphosphine) palladium(II) dichloride (39.3 mg, 0.056 mmol) were each rapidly added in sequence to a suspension of 7-chloro-5-methyl-2-[2-(1-methyl-1H-benzoimidazol-2-yl)-ethyl]-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dione (200 mg, 0.561 mmol, see Example c8)) and pyridin-3-ylboronic acid (103 mg, 0.841 mmol) in DMF (3 ml)/water (0.600 ml). The reaction was heated in a microwave at about 120° C. for about 20 min. The reaction was cooled to r.t., DCM (15 ml) and DMF (1 ml) were added, the resulting mixture was filtered and the filtrate was concentrated by evaporating DCM. The concentrate was cooled to r.t., the crystallized solid was filtered off, washed with water and dried to afford the title compound (50 mg, 0.125 mmol, 22.33% yield).

Workup

  1. temperatureThe reaction was cooled to r.t.
  2. filtrationthe resulting mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customby evaporating DCM
  5. temperatureThe concentrate was cooled to r.t.
  6. filtrationthe crystallized solid was filtered off
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-4466bf6fae7e446c95c97afc199a8994
Source dataset
uspto-grants-2015_10
Patent number
US09163019B2

Reaction notes

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