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

HRID 1752628Notes

Reaction equation

HRID 1752628 reaction equation
[C:1]([O-:4])([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:23]=[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]4[CH:30]=3)[C:18](=[O:19])[C:9]=12.[N:31]1[CH:36]=CC=[C:33](B(O)O)[CH:32]=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>[N:23]1[C:22]([CH2:21][CH2:20][N:17]2[C:18](=[O:19])[C:9]3[C:10](=[CH:11][N:12]([CH3:15])[C:13](=[O:14])[C:8]=3[N:31]3[CH2:36][CH2:1][O:4][CH2:33][CH2:32]3)[CH2:16]2)=[CH:30][N:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=12

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 904219587-Chloro-2-(2-imidazo[1,2-a]pyridin-2-yl-ethyl)-5-methyl-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dione

Product 1

HCID 862962742-(2-Imidazo[1,2-a]pyridin-2-yl-ethyl)-5-methyl-7-morpholin-4-yl-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dioneYield 35.6%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
120 °C

Procedure

K2CO3 (121 mg, 0.875 mmol) and bis(triphenylphosphine) palladium(II) dichloride (20.48 mg, 0.029 mmol) were each rapidly added in sequence to a suspension of 7-chloro-2-(2-imidazo[1,2-a]pyridin-2-yl-ethyl)-5-methyl-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dione (100 mg, 0.292 mmol, see Example c5)) and pyridin-3-ylboronic acid (53.8 mg, 0.438 mmol) in DMF (1 ml)/water (0.200 ml). The reaction mixture 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 and dried to afford the title compound (40 mg, 0.104 mmol, 35.6% 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
  7. customdried

Sources & evidence

ORD record
ord-64e2972ccd8b4c83b7d0c5d4be735eaa
Source dataset
uspto-grants-2015_10
Patent number
US09163019B2

Reaction notes

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