2,6-Di-tert-butyl-4-methylphenol → 4-(4-Vinyl-5-isoquinolyl)amino-1-(tert-butoxycarbonyl)piperidine

HRID 1373064

反応式

HRID 1373064 の反応式
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[CH:5]=[N:4][CH:3]=1.[CH2:26](C([Sn])=C(CCCC)CCCC)[CH2:27]CC.C(C1C(O)=C(C(C)(C)C)C=C(C)C=1)(C)(C)C.[F-].[K+]>C1(C)C=CC=CC=1.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>[CH:26]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[CH:5]=[N:4][CH:3]=1)=[CH2:27]

参加物

7

反応物 4

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 522689Potassium FluorideHCID 219799724-(4-Bromo-5-isoquinolyl)amino-1-(tert-butoxycarbonyl)piperidineHCID 53438229Tri(butyl)vinyltin

生成物 1

HCID 219799424-(4-Vinyl-5-isoquinolyl)amino-1-(tert-butoxycarbonyl)piperidine

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

A suspension of Intermediate 6 (8.00 g), tri(n-butyl)vinyltin (8.63 ml), tetrakis(triphenylphosphine)palladium(0) (455 mg), and 2,6-di-tert-butyl-p-cresol (8.7 mg) in toluene (120 ml) was stirred at 110° C. for 2 hours. The reaction mixture was cooled to room temperature, then added with 10% aqueous potassium fluoride (120 ml), and stirred for 15 hours. After the precipitates were removed by filtration, the organic layer was separated, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to obtain the title compound (6.72 g).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringstirred for 15 hours
  3. customAfter the precipitates were removed by filtration
  4. customthe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-fdeb0d8ab2bd48f9bf688e687a0f3bb3
出典データセット
uspto-grants-2007_01
特許番号
US07160894B2

関連ノート

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