Methanol → 6-cyano-3-methyl-1-(1-methylethyl)-1H-indole-4-carboxylic acid

HRID 1477058

反応式

HRID 1477058 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([C:16]([O:18]C)=[O:17])[C:6]2[C:7]([CH3:15])=[CH:8][N:9]([CH:12]([CH3:14])[CH3:13])[C:10]=2[CH:11]=1)#[N:2].CO.[OH-].[Na+]>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([C:16]([OH:18])=[O:17])[C:6]2[C:7]([CH3:15])=[CH:8][N:9]([CH:12]([CH3:14])[CH3:13])[C:10]=2[CH:11]=1)#[N:2]

参加物

5

反応物 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67467281methyl 6-cyano-1-isopropyl-3-methyl-1H-indole-4-carboxylate

生成物 1

HCID 674680896-cyano-3-methyl-1-(1-methylethyl)-1H-indole-4-carboxylic acid収率 64.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a 50 ml round bottom was added methyl 6-cyano-3-methyl-1-(1-methylethyl)-1H-indole-4-carboxylate (230 mg, 0.897 mmol), followed by methanol (1 mL) and THF (1 mL). To the solution was added 3 M NaOH (0.449 mL, 2.69 mmol). The reaction stirred at rt for 20 h. The reaction was evaporated and treated with acidic water to pH 5. A brown solid crashed out and was collected by filtration. The solid was an impurity. The pH of the liquid was adjusted to 3 and the liquid was evaporated leaving a residue. Trituration of the residue with water, followed by filtration yielded 6-cyano-3-methyl-1-(1-methylethyl)-1H-indole-4-carboxylic acid (155 mg, 0.576 mmol, 64.2% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-δ6) δ ppm 13.16 (br. s., 1H) 8.33 (s, 1H) 7.78 (s, 1H) 7.66 (s, 1H) 4.81-4.98 (m, 1H) 2.33 (s, 4H) 1.45 (d, J=6.57 Hz, 6H). MS(ES) [M+H]+ 243.3.

後処理

  1. customThe reaction was evaporated
  2. additiontreated with acidic water to pH 5
  3. filtrationwas collected by filtration
  4. customthe liquid was evaporated
  5. customleaving a residue
  6. filtrationTrituration of the residue with water, followed by filtration

出典と根拠

ORDレコード
ord-8c002b35b1184369bbe47cefea563c95
出典データセット
uspto-grants-2016_08
特許番号
US09402836B2

関連ノート

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