Ethyl bromoacetate → 2-((1-methyl-1H-indazol-6-yl)oxy)acetic acid

HRID 1429447

反応式

HRID 1429447 の反応式
[H-].[Na+].[CH3:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=2)[CH:6]=[N:5]1.Br[CH2:15][C:16]([O:18]CC)=[O:17]>CN(C=O)C.O>[CH3:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH2:15][C:16]([OH:18])=[O:17])[CH:11]=2)[CH:6]=[N:5]1

参加物

6

反応物 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 1355032231-methyl-1H-indazol-6-ol

生成物 1

HCID 846739652-((1-methyl-1H-indazol-6-yl)oxy)acetic acid収率 72%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of NaH (146 mg, 6.06 mmol) in DMF (3 mL) was added 1-methyl-1H-indazol-6-ol (300 mg, 2.02 mmol) at 25° C. After stirring for 5 minutes, ethyl 2-bromoacetate (406 mg, 2.43 mmol) was added and stirred for 16 h at 25° C. The mixture was then diluted with water (50 mL) and washed with ethyl acetate (2×20 mL). The water layer was then acidified by adding with 2N HCL until pH3 and then extracted with ethylacetate (2×20 ml). The combined organic layers were washed with brine (30 mL), dried over Na2SO4 and concentrated to give the crude product (300 mg, 63.4%) as colorless oil. It was used in next step without further purification. LCMS (m/z): 207.1 (M+1).

後処理

  1. stirringstirred for 16 h at 25° C
  2. washwashed with ethyl acetate (2×20 mL)
  3. additionby adding with 2N HCL until pH3
  4. extractionextracted with ethylacetate (2×20 ml)
  5. washThe combined organic layers were washed with brine (30 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-6e45124253ff4138a913fa58541dea96
出典データセット
uspto-grants-2015_01
特許番号
US08940726B2

関連ノート

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