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N-Methylcyclohexylamine → N-cyclohexyl-5-fluoro-N-methyl-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-amine

HRID 1696207
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HRID 1696207 반응식
Cl[C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[N:9]([Si:12]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])[CH:10]=[CH:11][C:3]=12.[CH3:22][NH:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.CC(C)([O-])C.[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(CCC)=CC(CCC)=CC=2CCC)CCCCC1>CC([O-])=O.CC([O-])=O.[Pd+2].O1CCOCC1>[CH:24]1([N:23]([CH3:22])[C:2]2[C:3]3[CH:11]=[CH:10][N:9]([Si:12]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])[C:4]=3[N:5]=[CH:6][C:7]=2[F:8])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1
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참가 물질

7

반응물 4

HCID 7514N-MethylcyclohexylamineHCID 21081571Dicyclohexyl(2',4',6'-tripropyl-[1,1'-biphenyl]-2-yl)phosphineHCID 23676156Sodium t-butoxideHCID 534382514-Chloro-5-fluoro-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 67278086N-cyclohexyl-5-fluoro-N-methyl-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-amine

시약·촉매·용매

2
HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

A mixture of 4-chloro-5-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (250 mg), N-methylcyclohexanamine (306 μl), Pd(OAc)2(17 mg), sodium tert-butoxide (176 mg), 2-dicyclohexylphosphino-2′,4′,6′-tri-1-propyl-1,1′-biphenyl (73 mg) and 1,4-dioxane (2.5 mL) was evacuated and backfield with N2 three times, then degassed with N2 for 10 minutes. The mixture was heated at 100° C. for 2.5 hours. After cooling to ambient temperature, the reaction mixture was concentrated. Purification of the crude product by column chromatography (silica gel, n-hexane:EtOAc=1:50) afforded N-cyclohexyl-5-fluoro-N-methyl-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-amine (53 mg) as a colorless solid.

후처리

  1. customwas evacuated
  2. customdegassed with N2 for 10 minutes
  3. temperatureAfter cooling to ambient temperature
  4. concentrationthe reaction mixture was concentrated
  5. customPurification of the crude product by column chromatography (silica gel, n-hexane:EtOAc=1:50)

출처 및 근거

ORD 기록
ord-68073a08ca904e9a974dca3ee63f2326
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163767B2

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