3-Methyl-4-pyridinamine → 2-Ethyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid (3-methyl-pyridin-4-yl)amide

HRID 564736ノート

反応式

HRID 564736 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH3:8].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[N+](C1C=CC([O:28][C:29]([C:31]2[C:32]3[CH:41]=[C:40]([CH2:42][CH3:43])[O:39][C:33]=3[C:34]([O:37][CH3:38])=[N:35][CH:36]=2)=O)=CC=1)([O-])=O>CN(C)C=O>[CH3:8][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[NH:1][C:29]([C:31]1[C:32]2[CH:41]=[C:40]([CH2:42][CH3:43])[O:39][C:33]=2[C:34]([O:37][CH3:38])=[N:35][CH:36]=1)=[O:28]

参加物

5

反応物 3

HCID 748113-Methyl-4-pyridinamineHCID 2724254Sodium bis(trimethylsilyl)amideHCID 541193452-Ethyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester

生成物 1

HCID 540972802-Ethyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid (3-methyl-pyridin-4-yl)amide収率 36.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 4-amino-3-methylpyridine (76 mg) in dry N,N-dimethylformamide (20 ml) was stirred at 0° C. under an atmosphere of dry nitrogen. Sodium bis(trimethylsilyl)amide (1.0M solution in tetrahydrofuran, 0.77 ml) was added and stirring continued at 0° C. for 10 minutes. 2-Ethyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester (0.20 g) was added and stirring continued at room temperature for 90 minutes. The solvent was then removed in vacuo, the residue taken up in water (100 ml) and extracted with ethyl acetate (3×75 ml). The combined organic extracts were washed with water (100 ml) then brine (50 ml), dried over magnesium sulfate, filtered and the solvent removed in vacuo. Purification by column chromatography on silica eluting with ethyl acetate followed by trituration with diethyl ether gave the title compound (66 mg) as a white solid.

後処理

  1. stirringstirring
  2. waitcontinued at room temperature for 90 minutes
  3. customThe solvent was then removed in vacuo
  4. extractionextracted with ethyl acetate (3×75 ml)
  5. washThe combined organic extracts were washed with water (100 ml)
  6. dry with materialbrine (50 ml), dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customPurification by column chromatography on silica eluting with ethyl acetate

出典と根拠

ORDレコード
ord-c32e2dc40a06489ea8f0359f84e7a8d1
出典データセット
uspto-grants-2001_01
特許番号
US06169090A

反応ノート

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