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Cesium carbonate → HCID 86679614, 화합물

HRID 577668
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인쇄 미리보기

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HRID 577668 반응식
Cl[C:2]1[N:3]=[C:4]([O:19][C:20]2[CH:21]=[C:22]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH:23]=[CH:24][CH:25]=2)[C:5]2[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=2[N:7]=1.[CH3:34][N:35]([CH3:44])[CH2:36][CH2:37][N:38]1[CH:42]=[C:41]([NH2:43])[CH:40]=[N:39]1.C([O-])([O-])=O.[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.[Cl-].[Na+].O.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]>[C:29]([O:28][C:27](=[O:33])[NH:26][C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([O:19][C:4]2[C:5]3[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=3[N:7]=[C:2]([NH:43][C:41]3[CH:40]=[N:39][N:38]([CH2:37][CH2:36][N:35]([CH3:44])[CH3:34])[CH:42]=3)[N:3]=2)[CH:21]=1)([CH3:32])([CH3:31])[CH3:30]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 283739571-(2-(Dimethylamino)ethyl)-1H-pyrazol-4-amineHCID 86679612tert-butyl (3-((2-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)phenyl)carbamate

생성물 1

HCID 86679614HCID 86679614, 화합물

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
140 °C

실험 절차

To a solution of tert-butyl {3-[(2-chloro-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy]phenyl}carbamate (300 mg, 0.61 mmol) in 1,4-dioxane (4 mL) in a microwave vial was added 1-[2-(dimethylamino)ethyl]-1H-pyrazol-4-amine (94.1 mg, 0.61 mmol) followed by Cs2CO3 (298 mg, 0.915 mmol), Pd2(dba)3 (8.2 mg, 0.009 mmol) and Xantphos (5.4 mg, 0.009 mmol) and the mixture heated in the microwave to 140° C. for 45 min. The reaction was cooled to rt and brine (20 mL) was added and the mixture was extracted with EtOAc (three×10 mL). The combined extracts were dried over MgSO4, filtered and stripped to give the title compound as a dark oil that was taken on to the next step with no purification. m/z (ESI+) for C30H44N8O4Si 609.25 (M+H)+.

후처리

  1. temperatureThe reaction was cooled to rt
  2. extractionthe mixture was extracted with EtOAc (three×10 mL)
  3. dry with materialThe combined extracts were dried over MgSO4
  4. filtrationfiltered

출처 및 근거

ORD 기록
ord-343c49ba68d946238ebe8bda71a4f65b
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09040547B2

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