2-Bromopyridine → 3-(2,3-Dihydro-benzofuran-5-yl)-2-pyridin-2-yl-1,2,3,4-tetrahydro-pyrrolo[3,4-b]quinolin-9-one

HRID 988331Notes

Reaction equation

HRID 988331 reaction equation
Cl.[O:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]3[C:15]4[NH:16][C:17]5[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=5[C:23](=[O:24])[C:14]=4[CH2:13][NH:12]3)=[CH:10][C:5]=2[CH2:4][CH2:3]1.Br[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]3[C:15]4[NH:16][C:17]5[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=5[C:23](=[O:24])[C:14]=4[CH2:13][N:12]3[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)=[CH:10][C:5]=2[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 79732-BromopyridineHCID 634876Binap, (A+-)-HCID 22640325HCID 22640325, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 112804743-(2,3-Dihydro-benzofuran-5-yl)-2-pyridin-2-yl-1,2,3,4-tetrahydro-pyrrolo[3,4-b]quinolin-9-one

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

3-(2,3-dihydro-5-benzofuranyl)-1,2,3,4-tetrahydro-9H-pyrrolo[3,4-b]quinolin-9-one HCl (0.30 g, 0.88 mmol) and 2-bromo-pyridine (2 mL), Pd2dba3 (0.23 g, 0.25 mmol), BINAP (0.47 g, 0.75 mmol) and NaOtBu (0.66 g, 6.87 mmol) were stirred in 1,4-dioxane (4 mL) at 90° C. for 1 hour. The resulting mixture was concentrated and then filtered on a plug of Celite with CH2Cl2. Purification by preparative TLC (5% CH3OH/CH2Cl2) yielded the title product as a yellow solid.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. filtrationfiltered on a plug of Celite with CH2Cl2
  3. customPurification by preparative TLC (5% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-6148c855f91142fda08a4c5a5a7378df
Source dataset
uspto-grants-2003_10
Patent number
US06635638B2

Reaction notes

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