1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 3-[4-(benzyloxy)phenyl]-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 587544Notes

Reaction equation

HRID 587544 reaction equation
Cl[C:2]1[C:7]([NH:8][C:9](=[O:15])OC(C)(C)C)=[C:6]([CH3:16])[CH:5]=[CH:4][N:3]=1.Cl.[CH2:18]([O:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[Na+]>CC(O)C.C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:18]([O:25][C:26]1[CH:27]=[CH:28][C:29]([N:30]2[C:2]3=[N:3][CH:4]=[CH:5][C:6]([CH3:16])=[C:7]3[NH:8][C:9]2=[O:15])=[CH:31][CH:32]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

8

Reactant 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 27238314-Benzyloxyaniline hydrochlorideHCID 23676156Sodium t-butoxideHCID 58577713Tert-butyl (2-chloro-4-methylpyridin-3-yl)carbamate

Product 1

HCID 585772463-[4-(benzyloxy)phenyl]-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-oneYield 36.2%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of tert-butyl (2-chloro-4-methylpyridin-3-yl)carbamate (2.00 g), 4-(benzyloxy)aniline hydrochloride (2.91 g), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (381 mg), sodium t-butoxide (1.90 g) and Pd2(dba)3 (302 mg) in 2-propanol (6 mL) and toluene (24 mL) was stirred at 100° C. under N2 atmosphere for 24 h. The reaction mixture was concentrated in vacuo. The residue was dissolved in MeOH, and the precipitate was removed by filtration. The filtrate was concentrated and the residue was purified by column chromatography (NH silica gel, eluted with 15%-50% AcOEt in hexane) to give 3-[4-(benzyloxy)phenyl]-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (988 mg) as a colorless solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in MeOH
  3. customthe precipitate was removed by filtration
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by column chromatography (NH silica gel, eluted with 15%-50% AcOEt in hexane)

Sources & evidence

ORD record
ord-19448f1208b146c883768d8461b404c1
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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