4-Bromopyridine → tert-Butyl 4-(pyridin-4-yl)piperazine-1-carboxylate

HRID 46001

反応式

HRID 46001 の反応式
Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[N:8]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.CC([O-])(C)C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.[Cl-].[Na+].O.CC([O-])=O.CC([O-])=O.[Pd+2].O>[N:5]1[CH:6]=[CH:7][C:2]([N:11]2[CH2:10][CH2:9][N:8]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:13][CH2:12]2)=[CH:3][CH:4]=1

参加物

10

反応物 4

HCID 142684-BromopyridineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

生成物 1

HCID 57436818tert-Butyl 4-(pyridin-4-yl)piperazine-1-carboxylate収率 47%

試薬・触媒・溶媒 5

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a degassed solution of 4-bromopyridine (1 equiv.), tert-butyl piperazine-1-carboxylate (16 mmol, 1.2 equiv.) and NaOtBu (3.4 equiv.) in toluene were added Pd(OAc)2 (2 mol %) and BINAP (1 mol %) and the resulting solution was refluxed for 3 h. The reaction mixture was cooled, diluted with ethyl acetate and given water and brine washes respectively. The organic layer was dried over sodium sulfate, the solvent removed in vacuo and the crude product purified by column chromatography (silica). Yield: 47%.

後処理

  1. temperaturethe resulting solution was refluxed for 3 h
  2. temperatureThe reaction mixture was cooled
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent removed in vacuo
  5. customthe crude product purified by column chromatography (silica)

出典と根拠

ORDレコード
ord-1fb23cebb0544832ac7e9595990b2180
出典データセット
uspto-grants-2013_09
特許番号
US08541573B2

関連ノート

読み込み中…