Potassium Carbonate → 10-[4-(1H-benzimidazol-2-yloxy)phenyl]-6,7,8,9-tetrahydropyrido[2,3-b]indolizine

HRID 573285노트

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HRID 573285 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:24]=[CH:23][C:12]([O:13][C:14]3[NH:18][C:17]4[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=4[N:15]=3)=[CH:11][CH:10]=2)O1.Br[C:27]1[C:28]2[N:39]=[CH:38][CH:37]=[CH:36][C:29]=2[N:30]2[C:35]=1[CH2:34][CH2:33][CH2:32][CH2:31]2.C([O-])([O-])=O.[K+].[K+]>COCCOC.O.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>[NH:18]1[C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[N:15]=[C:14]1[O:13][C:12]1[CH:11]=[CH:10][C:9]([C:27]2[C:28]3[N:39]=[CH:38][CH:37]=[CH:36][C:29]=3[N:30]3[C:35]=2[CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:24][CH:23]=1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 6672788310-Bromo-6,7,8,9-tetrahydropyrido[2,3-b]indolizineHCID 866889652-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-1H-benzimidazole

생성물 1

HCID 6672806310-[4-(1H-benzimidazol-2-yloxy)phenyl]-6,7,8,9-tetrahydropyrido[2,3-b]indolizine수율 13.2%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
150 °C

실험 절차

To a suspension of 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-1H-benzo[d]imidazole (320 mg), 10-bromo-6,7,8,9-tetrahydropyrido[2,3-b]indolizine (217 mg) and K2CO3 (119 mg) in DME (4 mL) and water (1 mL) was added Pd(PPh3)4 (100 mg). The mixture was heated at 150° C. for 40 min under microwave irradiation. The mixture was poured into water and extracted with AcOEt. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (43.4 mg).

후처리

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

출처 및 근거

ORD 기록
ord-14eb3b254427486893c5845be4f840de
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029536B2

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