Sodium Carbonate → 4-(1H-Indol-6-YL)benzoic acid

HRID 1785744노트

반응식

HRID 1785744 반응식
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.OB(O)[C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)C.CN(C=O)C>[NH:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([C:13]3[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=3)[CH:10]=2)[CH:6]=[CH:7]1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 6764936-Bromoindole

생성물 1

HCID 227303814-(1H-Indol-6-YL)benzoic acid

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

A mixture of 6-bromoindole (480 mg, 2.45 mmol), 4-(dihydroxyboryl)benzoic acid (406 mg, 2.45 mmol), Pd(dppf)Cl2CH2Cl2 (10 mg, 0.01 mmol), and 2M Na2CO3 (5.6 mL, 11.2 mmol) in a mixture of ethanol (4 mL) and DMF (7 mL) was heated to 100° C., stirred for 16 hours, filtered, and concentrated The concentrate was dissolved in ethyl acetate, washed sequentially with 1M H3PO4, water, and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 5% methanol/dichloromethane to provide the desired product. MS (ESI(−)) m/e 236 (M−H)−.

후처리

  1. filtrationfiltered
  2. concentrationconcentrated The concentrate
  3. dissolutionwas dissolved in ethyl acetate
  4. washwashed sequentially with 1M H3PO4, water, and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe concentrate was purified by flash column chromatography on silica gel with 5% methanol/dichloromethane

출처 및 근거

ORD 기록
ord-564003229d9d4c2b99027e9f3ba45c3d
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504512B2

반응 노트

불러오는 중…