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Dimethylcarbamoyl Chloride → 2-(Trimethylsilyl)ethyl 4-{4-[(dimethylcarbamoyl)oxy]phenyl}isoquinoline-6-carboxylate

HRID 1959955
ノート
印刷プレビュー

反応式

HRID 1959955 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])=[O:19])[CH:16]=3)[CH:11]=[N:10][CH:9]=2)=[CH:4][CH:3]=1.FC(F)(F)S(OC1C2C(=CC=C(C(OCC[Si](C)(C)C)=O)C=2)C=NC=1)(=O)=O.C(N(CC)CC)C.[CH3:61][N:62]([CH3:66])[C:63](Cl)=[O:64]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:61][N:62]([CH3:66])[C:63]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])=[O:19])[CH:16]=3)[CH:11]=[N:10][CH:9]=2)=[CH:6][CH:7]=1)=[O:64]
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 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 584957602-(Trimethylsilyl)ethyl 4-{[(trifluoromethyl)sulfonyl]oxy}isoquinoline-6-carboxylateHCID 667305282-(Trimethylsilyl)ethyl 4-(4-hydroxyphenyl)isoquinoline-6-carboxylate

生成物 1

HCID 667303722-(Trimethylsilyl)ethyl 4-{4-[(dimethylcarbamoyl)oxy]phenyl}isoquinoline-6-carboxylate収率 93.1%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

Into dichloromethane (6.5 mL), 2-(trimethylsilyl)ethyl 4-(4-hydroxyphenyl)isoquinoline-6-carboxylate (234 mg, 0.64 mmol) synthesized from 2-(trimethylsilyl)ethyl 4-{[(trifluoromethyl)sulfonyl]oxy}isoquinoline-6-carboxylate by the same method as in Example 8 (8a) was dissolved, to which triethylamine (178 μL, 1.28 mmol), 4-dimethylaminopyridine (23 mg, 0.19 mmol) and N,N-dimethylcarbamoyl chloride (88 μL, 0.96 mmol) were added, followed by stirring at room temperature for three hours. The resulting reaction liquid was concentrated under reduced pressure and the residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate, 100:0-50:50, V/V) to give the desired title compound (260 mg, yield 93%).

後処理

  1. additionwere added
  2. customThe resulting reaction liquid
  3. concentrationwas concentrated under reduced pressure
  4. customthe residue thus obtained
  5. customwas purified by silica gel column chromatography (hexane:ethyl acetate, 100:0-50:50, V/V)

出典と根拠

ORDレコード
ord-6d52655e74814895b97a43a611935b28
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08410273B2

反応ノート

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