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Potassium Iodide → methyl 8-(1-((3,5-difluorophenyl)(methyl)amino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate

HRID 1187228
ノート
印刷プレビュー

反応式

HRID 1187228 の反応式
[I-].[K+].Br[CH:4]([C:6]1[CH:7]=[C:8]([C:23]([O:25][CH3:26])=[O:24])[CH:9]=[C:10]2[C:15]=1[O:14][C:13]([N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)=[CH:12][C:11]2=[O:22])[CH3:5].[F:27][C:28]1[CH:29]=[C:30]([CH:33]=[C:34]([F:36])[CH:35]=1)[NH:31][CH3:32]>C(Cl)(Cl)Cl.CO>[F:27][C:28]1[CH:29]=[C:30]([N:31]([CH3:32])[CH:4]([C:6]2[CH:7]=[C:8]([C:23]([O:25][CH3:26])=[O:24])[CH:9]=[C:10]3[C:15]=2[O:14][C:13]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[CH:12][C:11]3=[O:22])[CH3:5])[CH:33]=[C:34]([F:36])[CH:35]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 4875Potassium IodideHCID 167203773,5-difluoro-N-methylanilineHCID 58234984methyl 8-(1-bromoethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate

生成物 1

HCID 58235022methyl 8-(1-((3,5-difluorophenyl)(methyl)amino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate収率 81.2%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒
HCID 6212Chloroform溶媒

実験手順

Potassium iodide (1.521 g, 9.16 mmol) was added to a suspension of methyl 8-(1-bromoethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate (3.3 g, 8.33 mmol, as described in Example 2.00) and 3,5-difluoro-N-methylaniline (3.58 g, 24.99 mmol) in CHCl3 (16 mL) and MeOH (4 mL). The mixture was stirred at RT over the weekend. The reaction mixture was concentrated to dryness and the resulting dark oil was triturated with diethyl ether to give a solid which was collected by filtration. This solid was suspended in water and pH was adjusted to 6-7 with 2N NaOH. The crude product was filtered and washed with ether, dried and purified by flash chromatography on silica gel eluting with 0 to 10% MeOH in DCM. The solvent was evaporated to dryness to afford methyl 8-(1-((3,5-difluorophenyl)(methyl)amino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate (3.1 g, 81%) as a white solid. Mass Spectrum: M+H+ 459.

後処理

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe resulting dark oil was triturated with diethyl ether
  3. customto give a solid which
  4. filtrationwas collected by filtration
  5. filtrationThe crude product was filtered
  6. washwashed with ether
  7. customdried
  8. custompurified by flash chromatography on silica gel eluting with 0 to 10% MeOH in DCM
  9. customThe solvent was evaporated to dryness

出典と根拠

ORDレコード
ord-4a9598f9683a43fba6c949f98eba6074
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08673906B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート