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Morpholine → HCID 86696258、化合物

HRID 2175139
ノート
印刷プレビュー

反応式

HRID 2175139 の反応式
C([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][C:9](Br)=[CH:8]2)(=O)C.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC([O-])(C)C.[K+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:16]1([C:9]2[CH:10]=[N:11][C:12]3[C:7]([CH:8]=2)=[CH:6][C:5]([OH:4])=[CH:14][CH:13]=3)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]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

7

反応物 4

HCID 8083MorpholineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23665647Potassium tert-butoxideHCID 685300473-Bromoquinolin-6-yl acetate

生成物 1

HCID 86696258HCID 86696258、化合物収率 44.7%

試薬・触媒・溶媒 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

A mixture of Intermediate A (0.8 g, 3.01 mmol), morpholine (1.048 g, 12.03 mmol), Pd2(dba)3 (0.275 g, 0.301 mmol), xantphos (0.305 g, 0.602 mmol) and KOtBu (0.337 g, 3.01 mmol) in toluene (15 ml) was bubbled with N2 for 15 min and then was heated at 100° C. for 5 h under MW radiation. The mixture was quenched with saturated aqueous NaHCO3 solution. The aqueous phase was extracted with DCM/IPA (10 ml, v/v=3/1) for 3 times. The combined extract was dried over anhydrous MgSO4. Filtered and concentrated, the residue was purified by silica gel chromatography to afford the title compound (0.31 g, 40.3% yield). LCMS (method B): [M+H]+=231, tR=1.1 min.

後処理

  1. customwas bubbled with N2 for 15 min
  2. customThe mixture was quenched with saturated aqueous NaHCO3 solution
  3. extractionThe aqueous phase was extracted with DCM/IPA (10 ml, v/v=3/1) for 3 times
  4. extractionThe combined extract
  5. dry with materialwas dried over anhydrous MgSO4
  6. filtrationFiltered
  7. concentrationconcentrated
  8. customthe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-91076422a1b44f498da70fdd12d9b1af
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09062045B2

反応ノート

読み込み中…

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