Hydrochloric Acid → 5-(biphenyl-4-yl)-6-chloro-1H-indole-3-carboxylic acid

HRID 1054670ノート

反応式

HRID 1054670 の反応式
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][C:15]=2[Cl:16])[NH:12][CH:11]=[C:10]3[C:17]([O:19]C)=[O:18])=[CH:3][CH:2]=1.[OH-].[Na+].Cl>CO>[C:1]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][C:15]=2[Cl:16])[NH:12][CH:11]=[C:10]3[C:17]([OH:19])=[O:18])=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86698673methyl 5-(biphenyl-4-yl)-6-chloro-1H-indole-3-carboxylate

生成物 1

HCID 866986745-(biphenyl-4-yl)-6-chloro-1H-indole-3-carboxylic acid収率 35%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of methyl 5-(biphenyl-4-yl)-6-chloro-1H-indole-3-carboxylate (50 mg, 0.14 mmol) in methanol (1.5 mL) and sodium hydroxide (1 M, 0.50 mmol, 0.50 mL) was stirred at 75° C. for 24 hours. The cooled reaction mixture was neutralized to an acidic pH with 1M HCl and extracted twice with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Methylene chloride was then added and solid precipitated. The slurry was stirred for 30 minutes then filtered and washed with methylene chloride and a small amount of ethyl acetate. The solids were dried in vacuo to provide the desired product as a tan solid (17 mg, 35% yield). MS (ES+) 348.1 (M+H)+. 1H NMR (500 MHz, DMSO-d6) δ 12.14 (br. s., 1H), 11.98 (br. s., 1H), 8.10 (d, J=2.93 Hz, 1H), 8.01 (s, 1H), 7.75 (t, J=8.42 Hz, 4H), 7.67 (s, 1H), 7.54 (d, J=8.05 Hz, 2H), 7.50 (t, J=7.56 Hz, 2H), 7.32-7.45 (m, 1H).

後処理

  1. customThe cooled reaction mixture
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. additionMethylene chloride was then added
  7. customsolid precipitated
  8. filtrationthen filtered
  9. washwashed with methylene chloride
  10. customThe solids were dried in vacuo

出典と根拠

ORDレコード
ord-0fe5504064934529a666cef7b712232b
出典データセット
uspto-grants-2016_07
特許番号
US09394285B2

反応ノート

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