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

HRID 1696207
ノート
印刷プレビュー

反応式

HRID 1696207 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒

2
HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-68073a08ca904e9a974dca3ee63f2326
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08163767B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート