Hydrochloric Acid → HCID 71087282、化合物

HRID 2405090ノート

反応式

HRID 2405090 の反応式
[Br:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([C:11]([O:13]C)=[O:12])=[CH:10][C:5]=2[N:4]([CH2:15][CH3:16])[CH:3]=1.Cl>CCO.[OH-].[Na+]>[Br:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:5]=2[N:4]([CH2:15][CH3:16])[CH:3]=1

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 67353647HCID 67353647、化合物

生成物 1

HCID 71087282HCID 71087282、化合物収率 98%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
80 °C

実験手順

A mixture of methyl 3-bromo-1-ethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (3A, 3.0 g, 11 mmol) in EtOH (10 ml) and 1N NaOH (10 ml) was stirred at 80° C. for 5 days. The reaction mixture was acidified with 1N HCl, concentrated in vacuo and dried to give 3-bromo-1-ethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylic acid (3B, 2.8 g, 10 mmol, 98% yield) as a pale brown powder. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.42 (t, J=7.20 Hz, 3H) 4.49 (q, J=7.33 Hz, 2H) 8.35 (s, 1H) 8.65 (s, 1H) 8.91 (s, 1H). 3F In a 200 ml round bottom flask, methyl 3-bromo-1-methyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (3E, 8.5 g, 32 mmol) was dissolved THF (50 ml) NaOH (32 ml, 63 mmol) solution was added to the mixture and the stirring continued at room temperature overnight. Another equivalent of base was added and the mixture was warmed with water bath to complete the reaction. Volatiles were removed in vacuo and the residue was cooled in an ice bath and neutralized with dilute HCl to pH 4.0-4.5. The precipitated product was collected by filtration to give the product 3-bromo-1-methyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylic acid (3F, 7.3 g, 91%).

後処理

  1. concentrationconcentrated in vacuo
  2. customdried

出典と根拠

ORDレコード
ord-1b4744aa8a0248f08b9171969993b7fe
出典データセット
uspto-grants-2014_08
特許番号
US08802695B2

反応ノート

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