methyl 1H-indole-4-carboxylate → HCID 54402352、化合物

HRID 1655056ノート

反応式

HRID 1655056 の反応式
C[Mg]Br.[NH:4]1[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([C:13]([O:15][CH3:16])=[O:14])[C:7]=2[CH:6]=[CH:5]1.[N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[CH2:27][O:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Cl)=[CH:31][CH:30]=1>C(OCCCC)CCC.CN(C)C=O>[CH3:16][O:15][C:13]([C:8]1[C:7]2[C:6]([CH2:33][C:32]3[CH:31]=[CH:30][C:29]([O:28][CH2:27][C:18]4[CH:19]=[CH:20][C:21]5[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=5)[N:17]=4)=[CH:36][CH:35]=3)=[CH:5][NH:4][C:12]=2[CH:11]=[CH:10][CH:9]=1)=[O:14]

参加物

6

反応物 3

HCID 2733668methyl 1H-indole-4-carboxylateHCID 147741632-(4-Chloromethylphenoxy)methylquinolineHCID 178418573HCID 178418573、化合物

生成物 1

HCID 54402352HCID 54402352、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8909Butyl ether溶媒

実験手順

A solution of methyl magnesium bromide in n-butyl ether (1.0M, 10.3 ml) was added dropwise to a solution of methyl indole-4-carboxylate (1.5 g) in dry dimethylformamide (15 ml) stirred under an atmosphere of nitrogen at room temperature. The mixture was stirred at room temperature for 20 minutes then a solution of 4-(quinolin-2-ylmethoxy)benzyl chloride (Example 1a) (2.35 g) in dry dimethylformamide (10 ml) added dropwise. The mixture was stirred at room temperature overnight, concentrated in vacuo, diluted with ethyl acetate and washed with water and a saturated solution of ammonium chloride; the organic phase was dried, filtered and evaporated. The residue was purified by chromatography on flash silica, eluting with petroleum spirit 40°-60° C.--diethyl ether (1:1) to give the product as a white solid. A small quantity was crystallised from petroleum spirit 40°-60° C.--diethyl ether (1:1), m.p. 148°-150° C.

後処理

  1. stirringThe mixture was stirred at room temperature for 20 minutes
  2. stirringThe mixture was stirred at room temperature overnight
  3. concentrationconcentrated in vacuo
  4. additiondiluted with ethyl acetate
  5. washwashed with water
  6. customthe organic phase was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by chromatography on flash silica
  10. washeluting with petroleum spirit 40°-60° C.

出典と根拠

ORDレコード
ord-f3847ded8c884b36895affb2a38109c1
出典データセット
uspto-grants-1995_04
特許番号
US05410061

反応ノート

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