Lithium Hydroxide → 1-(5-Bromo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropane-1-carboxylic acid

HRID 710935ノート

反応式

HRID 710935 の反応式
[Br:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3([C:14]([O:16]CC)=[O:15])[CH2:13][CH2:12]3)[N:10]=[C:6]2[C:5]([O:19][CH3:20])=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1.CCOC(C)=O.O>[Br:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3([C:14]([OH:16])=[O:15])[CH2:13][CH2:12]3)[N:10]=[C:6]2[C:5]([O:19][CH3:20])=[CH:4][CH:3]=1

参加物

6

反応物 2

HCID 3939Lithium HydroxideHCID 89651597Ethyl 1-(5-bromo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxylate

生成物 1

HCID 867645081-(5-Bromo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropane-1-carboxylic acid収率 94%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To a solution of ethyl 1-(5-bromo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxylate (3.00 g, 8.82 mmol) in THF (25 mL) was added an aqueous 1 M solution of LiOH (25 mL). The mixture was stirred at 80° C. for 30 minutes, cooled to room temperature and diluted with EtOAc (50 mL) and water (50 mL). The organic phase was extracted with an aqueous 0.1 M solution of NaOH (25 mL) and the combined aqueous phases were acidified with conc. HCl to pH 0-1, and extracted four times with DCM (30 mL). Evaporation to dryness of the combined organic phases yielded the title compound (2.54 g, 94%). 1H NMR (DMSO, 400 MHz): δ=12.61 (s, 1H), 7.42 (d, 1H, J=8.3 Hz), 7.06 (d, 1H, 3=8.3 Hz), 3.97 (s, 3H), 1.53 (q, 2H, 3=3.9 Hz), 1.40 (q, 2H, J=3.9 Hz) ppm.

後処理

  1. temperaturecooled to room temperature
  2. extractionThe organic phase was extracted with an aqueous 0.1 M solution of NaOH (25 mL)
  3. extractionextracted four times with DCM (30 mL)
  4. customEvaporation to dryness of the combined organic phases

出典と根拠

ORDレコード
ord-f051b5ea1ef34c179c5394f4564268d4
出典データセット
uspto-grants-2015_11
特許番号
US09181248B2

反応ノート

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