1,2-Dimethoxyethane → 2-Methyl-1-(2-{4-[1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridin-3-yl]phenoxy}-1H-benzimidazol-1-yl)propan-2-ol

HRID 573358노트

반응식

HRID 573358 반응식
[CH3:1][C:2]([OH:30])([CH3:29])[CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[O:13][C:14]1[CH:19]=[CH:18][C:17](B2OC(C)(C)C(C)(C)O2)=[CH:16][CH:15]=1.Br[C:32]1[C:36]2=[N:37][CH:38]=[CH:39][CH:40]=[C:35]2[N:34]([CH:41]([CH3:43])[CH3:42])[N:33]=1.C([O-])([O-])=O.[Cs+].[Cs+].COCCOC>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.O>[CH3:29][C:2]([OH:30])([CH3:1])[CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[O:13][C:14]1[CH:19]=[CH:18][C:17]([C:32]2[C:36]3=[N:37][CH:38]=[CH:39][CH:40]=[C:35]3[N:34]([CH:41]([CH3:43])[CH3:42])[N:33]=2)=[CH:16][CH:15]=1

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 667280773-bromo-1-isopropyl-1H-pyrazolo[4,3-b]pyridineHCID 866889962-methyl-1-{2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-1H-benzimidazol-1-yl}propan-2-ol

생성물 1

HCID 866889952-Methyl-1-(2-{4-[1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridin-3-yl]phenoxy}-1H-benzimidazol-1-yl)propan-2-ol수율 68.5%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회

반응 조건

온도
140 °C

실험 절차

A mixture of 2-methyl-1-{2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-1H-benzimidazol-1-yl}propan-2-ol (237 mg), 3-bromo-1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridine (139 mg), Cs2CO3 (378 mg), Pd(PPh3)4 (20.1 mg), DME (5 mL), and water (1 mL) was stirred at 140° C. for 30 min under microwave irradiation. The reaction mixture was poured into water and extracted with AcOEt. The extract was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) and recrystallized from AcOEt/hexane to give the title compound (175 mg).

후처리

  1. extractionextracted with AcOEt
  2. washThe extract was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)
  6. customrecrystallized from AcOEt/hexane

출처 및 근거

ORD 기록
ord-32b93cae20c6465aa94e4faa541847c7
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029536B2

반응 노트

불러오는 중…