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

HRID 1095705노트

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HRID 1095705 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 into dioxane (74.1 ml, 18.5 mmol) and water (0.735 ml, 40.8 mmol) and heated to 100° C. overnight under nitrogen. The reaction was diluted with DCM and carbon (5 g) was added, followed by filtration. The filtrate was concentrated and then triturated with 1:1 EtOAc/MTBE (30 mL). The resulting solids were allowed to stir for 5 hours and then filtered to isolate of the desired product as a solid (5.4 g, 69% yield).

후처리

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

출처 및 근거

ORD 기록
ord-d24a19fa3df546af901b43d1c199f0d9
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138181B2

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