Tetravinylstannane → 2-chloro-N-(1H-indazol-6-yl)-5-vinyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 645704

반응식

HRID 645704 반응식
[Cl:1][C:2]1[N:3]=[C:4]([NH:22][C:23]2[CH:31]=[C:30]3[C:26]([CH:27]=[N:28][NH:29]3)=[CH:25][CH:24]=2)[C:5]2[C:10](I)=[CH:9][N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:6]=2[N:7]=1.[CH:32]([Sn](C=C)(C=C)C=C)=[CH2:33]>CN(C)C=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>[Cl:1][C:2]1[N:3]=[C:4]([NH:22][C:23]2[CH:31]=[C:30]3[C:26]([CH:27]=[N:28][NH:29]3)=[CH:25][CH:24]=2)[C:5]2[C:10]([CH:32]=[CH2:33])=[CH:9][N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:6]=2[N:7]=1

참가 물질

5

반응물 2

HCID 66189TetravinylstannaneHCID 866280402-chloro-N-(1H-indazol-6-yl)-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

생성물 1

HCID 866280412-chloro-N-(1H-indazol-6-yl)-5-vinyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine수율 29.6%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a solution of 2-chloro-N-(1H-indazol-6-yl)-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.45 g, 0.8 mmol) in dimethylformamide (2.0 mL) was added tetravinyltin (0.29 mL, 1.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) (0.092 g, 0.08 mmol). After degassing, the mixture was heated at 60° C. for 15 h. before it was diluted with EtOAc, and washed sequentially with Sat. NaHCO3 and brine. The organic extract was dried over Na2SO4 and concentrated to give a crude residue. Purification by flash column chromatography (Hexane/EtOAc=1:1) gave 2-chloro-N-(1H-indazol-6-yl)-5-vinyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.11 g).

후처리

  1. customAfter degassing
  2. additionwas diluted with EtOAc
  3. washwashed sequentially with Sat. NaHCO3 and brine
  4. extractionThe organic extract
  5. dry with materialwas dried over Na2SO4
  6. concentrationconcentrated
  7. customto give a crude residue
  8. customPurification by flash column chromatography (Hexane/EtOAc=1:1)

출처 및 근거

ORD 기록
ord-f5ee33c6b49a4a03a14cc86261f53e97
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705004B2

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