Water → 8-(Benzyloxy)-2-(7-(2-methoxyethoxy)-imidazo[1,2-a]pyridin-3-yl)quinoline

HRID 1095723노트

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HRID 1095723 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16](Cl)[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][O:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][N:28]2[CH:31]=[CH:32][N:33]=[C:27]2[CH:26]=1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1.O>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([C:31]1[N:28]3[CH:29]=[CH:30][C:25]([O:24][CH2:23][CH2:22][O:21][CH3:20])=[CH:26][C:27]3=[N:33][CH:32]=1)[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

9

반응물 5

HCID 962WaterHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 220422348-(Benzyloxy)-2-chloroquinolineHCID 583692597-(2-Methoxyethoxy)imidazo[1,2-a]pyridine

생성물 1

HCID 667814488-(Benzyloxy)-2-(7-(2-methoxyethoxy)-imidazo[1,2-a]pyridin-3-yl)quinoline수율 69%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 178418397HCID 178418397, 화합물촉매HCID 6344Dichloromethane용매

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온도
100 °C

실험 절차

8-(Benzyloxy)-2-chloroquinoline (5.0 g, 18.5 mmol), 7-(2-methoxyethoxy)-imidazo[1,2-a]pyridine (3.56 g, 18.5 mmol), Pd(PPh3)4 (1.07 g, 0.927 mmol), K2CO3 (5.12 g, 37.1 mmol), and Pd(OAc)2 (0.208 g, 0.927 mmol) were added to dioxane (74.1 ml, 18.5 mmol) and water (0.735 ml, 40.8 mmol) and the reaction mixture was heated to 100° C. overnight under nitrogen. The reaction was diluted with DCM and 5 g of carbon were added followed by filtration. The slurry was concentrated and the filtrate was triturated with 1:1 EtOAc/MTBE (30 mL). The resulting solids were stirred for 5 hours and then filtered to isolate the desired product as a solid (5.4 g, 69% yield).

후처리

  1. additionwere added
  2. filtrationfollowed by filtration
  3. concentrationThe slurry was concentrated
  4. customthe filtrate was triturated with 1:1 EtOAc/MTBE (30 mL)
  5. filtrationfiltered

출처 및 근거

ORD 기록
ord-84c16d0e761f49c1b8643adc94449a7d
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138181B2

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