Cesium carbonate → 9-(Cyclopropylmethyl)-8-fluoro-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine

HRID 875979

반응식

HRID 875979 반응식
C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:50]1[C:51]([F:68])=[N:52][CH:53]=[CH:54][C:55]=1[C:56]1[C:57]([NH:63][CH2:64][CH:65]2[CH2:67][CH2:66]2)=[N:58][C:59]([NH2:62])=[N:60][CH:61]=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:65]1([CH2:64][N:63]2[C:57]3[N:58]=[C:59]([NH2:62])[N:60]=[CH:61][C:56]=3[C:55]3[CH:54]=[CH:53][N:52]=[C:51]([F:68])[C:50]2=3)[CH2:67][CH2:66]1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 582995575-(3-Bromo-2-fluoropyridin-4-yl)-N4-(cyclopropylmethyl)pyrimidine-2,4-diamine

생성물 1

HCID 583000719-(Cyclopropylmethyl)-8-fluoro-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine수율 79%

시약·촉매·용매 1

HCID 9811564Bis(dibenzylideneacetone)palladium촉매

반응 조건

온도
100 °C

실험 절차

To a vacuum to argon purged vial containing 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.017 g, 0.030 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.014 g, 0.015 mmol), cesium carbonate (0.19 g, 0.59 mmol) and compound 240 (0.100 g, 0.30 mmol) was added degassed dioxane (2.00 mL). The reaction was stirred at 100° C. After 4 h, the reaction was cooled and applied directly to silica. Silica gel chromatography (gradient elution 40 to 90% ethyl acetate in hexanes) afforded compound 241 (0.060 g, 79% yield). 1H NMR (500 MHz, CDCl3) δ ppm 0.45-0.57 (m, 4 H) 1.34-1.47 (m, 1 H) 4.32 (d, J=7.09 Hz, 2 H) 5.46 (br. s., 2 H) 7.68 (dd, J=5.26, 2.81 Hz, 1 H) 8.02 (dd, J=5.13, 1.71 Hz, 1 H) 8.93 (s, 1 H).

후처리

  1. additionwas added
  2. customdegassed dioxane (2.00 mL)
  3. temperaturethe reaction was cooled
  4. washSilica gel chromatography (gradient elution 40 to 90% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-29f3bc1f545f435782629b536169336e
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980903B2

연결된 노트

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