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Trifluoroacetic acid → 6-tert-butyl 2-methyl 7,8-dihydropyrrolo[3,2-e]indole-2,6(3H)-dicarboxylate

HRID 1183813
ノート
印刷プレビュー

反応式

HRID 1183813 の反応式
[CH:1]1[C:5]2=[C:6]3[C:10]([CH:11]=[CH:12][C:4]2=[N:3][C:2]=1[C:13]([O:15][CH3:16])=[O:14])=[N:9][CH:8]=[CH:7]3.N1[CH2:22][CH2:21][CH2:20]CC1.C1C2=C3C(=CC=C2NC1)NC([C:35]([O:37]C)=[O:36])=C3.[C:39](O)(C(F)(F)F)=O>CN(C=O)C.CCN(C(C)C)C(C)C>[C:21]([O:37][C:35]([N:9]1[C:10]2[C:6](=[C:5]3[C:4](=[CH:12][CH:11]=2)[NH:3][C:2]([C:13]([O:15][CH3:16])=[O:14])=[CH:1]3)[CH2:7][CH2:8]1)=[O:36])([CH3:20])([CH3:22])[CH3:39]
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 6422Trifluoroacetic acidHCID 8082PiperidineHCID 15480266Methyl 3,6,7,8-tetrahydropyrrolo[3,2-e]indole-2-carboxylateHCID 178496869HCID 178496869、化合物

生成物 1

HCID 151147736-tert-butyl 2-methyl 7,8-dihydropyrrolo[3,2-e]indole-2,6(3H)-dicarboxylate

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
3 回
HCID 81531Diisopropylethylamine溶媒

反応条件

温度
25 °C

実験手順

A solution of 3 (15 mg, 0.014 mmol) in DMF (2 mL) was treated with 5% piperidine in DMF (2 mL) and the reaction mixture was stirred for 10 min at 25° C. The crude product was precipitated with diethyl ether and used for the next step without further purification. The crude product was dissolved in DMF (3 mL) followed by the addition of 4 (25 mg, 0.025 mmol) in DMF (2 mL) and DIEA (20 uL). The reaction mixture was stirred for 2 hrs at room temperature. TFA was added to the reaction mixture and the reaction mixture was stirred at room temperature for 45 min to yield compound 5 as indicated by analytical HPLC. Crude product was purified by Prep HPLC (SymmetrPrep C18, 7 μm, 19×150 mm column), eluted at 10 ml/min (0.01% TFA in water/acetonitrile) with a gradient: 10% acetonitrile in 5 min, 10% to 50% acetonitrile in 15 min, maintaining 50% acetonitrile in 5 min, 50% to 100% acetonitrile in 5 min, to obtain 5 (3 mg, 94%). MS: (MH)+ 889.

後処理

  1. customThe crude product was precipitated with diethyl ether
  2. customused for the next step without further purification
  3. dissolutionThe crude product was dissolved in DMF (3 mL)
  4. stirringThe reaction mixture was stirred for 2 hrs at room temperature
  5. stirringthe reaction mixture was stirred at room temperature for 45 min

出典と根拠

ORDレコード
ord-440b70ca10bb44bf8a49318adf694142
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08664407B2

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