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

HRID 338327노트

반응식

HRID 338327 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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 (1M, 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).

후처리

  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

출처 및 근거

ORD 기록
ord-7b94fa1b6dc043f7a62e08fa4638d145
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889730B2

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