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Potassium Phosphate, Tribasic → tert-butyl (3R)-3-({[3-(pyridin-4-yl)-1-trityl-1H-indazol-5-yl]carbonyl}amino)piperidine-1-carboxylate

HRID 1467338
ノート
印刷プレビュー

反応式

HRID 1467338 の反応式
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([NH:13][C@@H:14]3[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]3)=[O:12])[CH:9]=2)[N:4]([C:27]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].Cl[Pd]Cl>[N:16]1[CH:17]=[CH:18][C:19]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:11]([NH:13][C@@H:14]4[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]4)=[O:12])[CH:9]=3)[N:4]([C:27]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:3]=2)=[CH:14][CH:15]=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

5

反応物 2

HCID 62657Potassium Phosphate, TribasicHCID 70652333(R)-tert-butyl 3-(3-bromo-1-trityl-1H-indazole-5-carboxamido)piperidine-1-carboxylate

生成物 1

HCID 86681283tert-butyl (3R)-3-({[3-(pyridin-4-yl)-1-trityl-1H-indazol-5-yl]carbonyl}amino)piperidine-1-carboxylate収率 190%

試薬・触媒・溶媒 2

HCID 24290Palladium Chloride触媒
HCID 635956
Ferrocene-1,1'-bis-(diphenylphosphine)
触媒

反応条件

温度
80 °C

実験手順

A flask was charged with tert-butyl (3R)-3-{[(3-bromo-1-trityl-1H-indazol-5-yl)carbonyl]amino}piperidine-1-carboxylate (4.00 g, 6.01 mmoles), potassium phosphate (2.05 g, 9.66 mmoles) and 1,1′-Bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (160.0 mg, 0.219 mmoles). The flask was put under an atmosphere of argon (3× vacuum/argon cycle) and degassed dioxane (20 mL) and water (5 mL) were injected. The reaction was heated to 80° C. for 16 hours and was then allowed to cool to ambient temperature. The resulting solution was poured into water (100 mL) and the aqueous emulsion was washed three times with chloroform/isopropanol (4:1, 50 mL portions). The combined organic washings were dried over sodium sulfate, filtered and concentrated to dryness. Flash chromatography (gradient 0-15% dichloromethane/methanol) to yield tert-butyl (3R)-3-({[3-(pyridin-4-yl)-1-trityl-1H-indazol-5-yl]carbonyl}amino)piperidine-1-carboxylate as a white solid (3.79 g, 95%).

後処理

  1. customdegassed dioxane (20 mL) and water (5 mL)
  2. temperatureto cool to ambient temperature
  3. additionThe resulting solution was poured into water (100 mL)
  4. washthe aqueous emulsion was washed three times with chloroform/isopropanol (4:1, 50 mL portions)
  5. dry with materialThe combined organic washings were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-702c3980382f4b7c952dc961ee692bb5
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08999957B2

反応ノート

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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