Sodium Hydroxide → 3-(1H-Indol-1-yl)-2-phenylquinoxaline-6-carboxylic acid

HRID 716997노트

반응식

HRID 716997 반응식
[N:1]1([C:10]2[C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:12][C:13]3[C:18]([N:19]=2)=[CH:17][C:16]([C:20]([O:22]C)=[O:21])=[CH:15][CH:14]=3)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[Na+]>CO.O>[N:1]1([C:10]2[C:11]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[N:12][C:13]3[C:18]([N:19]=2)=[CH:17][C:16]([C:20]([OH:22])=[O:21])=[CH:15][CH:14]=3)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 67042171Methyl 3-(1H-indol-1-yl)-2-phenylquinoxaline-6-carboxylate

생성물 1

HCID 509912123-(1H-Indol-1-yl)-2-phenylquinoxaline-6-carboxylic acid

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

Into a 50-mL round-bottom flask, was placed a solution of methyl 3-(1H-indol-1-yl)-2-phenylquinoxaline-6-carboxylate (40 mg, 0.11 mmol, 1.00 equiv) in methanol (10 mL). A solution of sodium hydroxide (21.1 mg, 0.53 mmol, 5.00 equiv) in H2O (2 mL) was added. The resulting solution was stirred for 2 hrs at 50° C. in an oil bath. The resulting mixture was concentrated in vacuo. The resulting solution was diluted with 20 mL of H2O. The pH value of the aqueous solution was adjusted to 4-5 with aq. 1N hydrogen chloride. The resulting solids were collected by filtration. The crude product (50 mL) was further purified by Flash-Prep-HPLC with the following conditions (IntelFlash-1): Column, silica gel; mobile phase, H2O/CH3CN=100:1 increasing to H2O/CH3CN=100:60 within 40 min; Detector, UV 254 nm. This resulted in 15 mg (38%) of 3-(1H-indol-1-yl)-2-phenylquinoxaline-6-carboxylic acid as a yellow solid.

후처리

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. additionThe resulting solution was diluted with 20 mL of H2O
  4. filtrationThe resulting solids were collected by filtration
  5. customThe crude product (50 mL) was further purified by Flash-Prep-HPLC with the following conditions (IntelFlash-1)
  6. waitmobile phase, H2O/CH3CN=100:1 increasing to H2O/CH3CN=100:60 within 40 min
  7. customThis resulted in 15 mg (38%) of 3-(1H-indol-1-yl)-2-phenylquinoxaline-6-carboxylic acid as a yellow solid

출처 및 근거

ORD 기록
ord-af0d67e992d24c3590862153df4db17f
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193693B2

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