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 587544ノート

反応式

HRID 587544 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 3776Isopropanol溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-19448f1208b146c883768d8461b404c1
出典データセット
uspto-grants-2016_01
特許番号
US09226921B2

反応ノート

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