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N,N-Dimethylpropargylamine → Dimethyl-[3-(1H-pyrrolo[2,3-b]pyridin-5-yl)-prop-2-ynyl]-amine

HRID 269482
ノート
印刷プレビュー

反応式

HRID 269482 の反応式
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH3:11][N:12]([CH3:16])[CH2:13][C:14]#[CH:15]>CN(C=O)C.C(Cl)Cl.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:11][N:12]([CH3:16])[CH2:13][C:14]#[C:15][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 2

HCID 81643N,N-DimethylpropargylamineHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 59832182Dimethyl-[3-(1H-pyrrolo[2,3-b]pyridin-5-yl)-prop-2-ynyl]-amine

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒
HCID 6228
Dimethylformamide
溶媒
HCID 6344Dichloromethane溶媒

実験手順

To a screw top tube, 8.1 mg (0.0425 mmoles) of CuI, 18 mg(0.0256 mmoles) of PdCl2(PPh3)2, and 207 mg (0.8483 mmoles) of 5-Bromo-1H-pyrrolo[2,3-b]pyridine were added. The dry solids were diluted with 1 ml of dry DMF and a stream of N2 was bubbled through the solution for 10 minutes and then 182.6 ul(1.7 mmoles) of Dimethyl-prop-2-ynyl-amine was added and the reaction was stirred in a sealed tube overnight at room temperature. The reaction was diluted with 10 ml of DCM and washed with saturated ammonium chloride solution. The organic layer was separated and dried with MgSO4, filtered, and concentrated to dryness yielding a crude material of 189 mg. MS showed a M+ ion of 200.05 which confirmed the structure above. The crude material was taken to the next step.

後処理

  1. customa stream of N2 was bubbled through the solution for 10 minutes
  2. washwashed with saturated ammonium chloride solution
  3. customThe organic layer was separated
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-40771809de4344e78270d7a21c6af945
出典データセット
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07446199B2

反応ノート

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