Iodoethane → 3-[4-(benzyloxy)phenyl]-6-chloro-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 1429978

반응식

HRID 1429978 반응식
Cl[C:2]1[C:7]([NH:8][C:9](=[O:15])OC(C)(C)C)=[CH:6][C:5]([Cl:16])=[CH:4][N:3]=1.[CH2:17]([O:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH3:32][C:33]1(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+].[H-].[Na+].C(I)C.[Cl-].[Cl-].[Ca+2]>C1(C)C=CC=CC=1.CN(C=O)C.CO.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].CC(O)C>[CH2:17]([O:24][C:25]1[CH:26]=[CH:27][C:28]([N:29]2[C:2]3=[N:3][CH:4]=[C:5]([Cl:16])[CH:6]=[C:7]3[N:8]([CH2:32][CH3:33])[C:9]2=[O:15])=[CH:30][CH:31]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

참가 물질

13

반응물 7

HCID 6340IodoethaneHCID 228604-BenzyloxyanilineHCID 24758Sodium hydrideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 5284359Calcium ChlorideHCID 23676156Sodium t-butoxideHCID 86660673Tert-butyl 2,5-dichloropyridin-3-ylcarbamate

생성물 1

HCID 585773703-[4-(benzyloxy)phenyl]-6-chloro-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one수율 247.5%

시약·촉매·용매 5

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 887Methanol용매HCID 1140Toluene용매HCID 3776Isopropanol용매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

The mixture of tert-butyl (2,5-dichloropyridin-3-yl)carbamate (7.0 g), 4-(benzyloxy)aniline (7.95 g), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (1.231 g), Pd2(dba)3 (0.974 g) and sodium tert-butoxide (3.58 g) in toluene (160 mL)-2-propanol (40.0 mL) was stirred at 100° C. under Ar overnight. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 0%-100% EtOAc in hexane) to give intermediate. To the intermediate in DMF (100 mL) were added NaH (3.19 g) and ethyl iodide (20.75 g). The mixture was stirred at room temperature under a dry atmosphere (CaCl2 tube) for 1 h. The reaction mixture was diluted with MeOH and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with 0%-50% EtOAc in hexane) to give 3-[4-(benzyloxy)phenyl]-6-chloro-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (2 g) as a colorless solid.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by column chromatography (silica gel, eluted with 0%-100% EtOAc in hexane)
  3. customto give intermediate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (NH silica gel, eluted with 0%-50% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-c2ab3139321147b69361ff6e1bc9e353
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940758B2

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