Potassium Fluoride → HCID 178428567、化合物

HRID 1748534ノート

反応式

HRID 1748534 の反応式
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][C:12]([C:15]2[N:20]=[CH:19][C:18]([NH2:21])=[CH:17][C:16]=2[CH3:22])=[CH:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[F-].[K+]>O1CCCC1.O.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[N:20]=[CH:19][C:18]([NH2:21])=[CH:17][C:16]=2[CH3:22])[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

参加物

7

反応物 2

HCID 522689Potassium FluorideHCID 866924826-(4-{[tert-Butyl(dimethyl)silyl]oxy}cyclohex-1-en-1-yl)-5-methylpyridin-3-amine

生成物 1

HCID 178428567HCID 178428567、化合物収率 89.4%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 6-(4-{[tert-butyl(dimethyl)silyl]oxy}-cyclohex-1-en-1-yl)-5-methylpyridin-3-amine (1.5 g) described in Reference Example 110, palladium acetate (211 mg) and potassium fluoride (1.09 g) in tetrahydrofuran (24 ml) and water (10 ml) was slowly added dropwise polymethylhydrosiloxane (PMHS) (1.12 ml) at room temperature with stirring, and then stirred at room temperature for 2 hours. After completion of the reaction, the reaction solution was diluted with diethyl ether, filtered through Celite, and then the filtrate was concentrated to half of the volume. Then, saturated brine was added thereto, the mixture was extracted with ethyl acetate, the obtained organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated in vacuo. The obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give the titled compound (1.35 g) as a light brown solid. MS (ESI) m/z: 321 (M+H)+.

後処理

  1. stirringstirred at room temperature for 2 hours
  2. customAfter completion of the reaction
  3. filtrationfiltered through Celite
  4. concentrationthe filtrate was concentrated to half of the volume
  5. additionThen, saturated brine was added
  6. extractionthe mixture was extracted with ethyl acetate
  7. dry with materialthe obtained organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated in vacuo
  9. customThe obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-b673e6b9d9144747a5695e2f91f0bcce
出典データセット
uspto-grants-2015_10
特許番号
US09150555B2

反応ノート

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