Diisopropylethylamine → 1-Benzhydryl-5-bromo-1H-indole-2-carboxylic Acid

HRID 987164

반응식

HRID 987164 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=[O:12])=[CH:5]2.CCN(C(C)C)C(C)C.Br[CH:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN1CCCC1=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:24]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([Br:1])=[CH:10][CH:9]=2)[CH:5]=[C:6]1[C:11]([OH:13])=[O:12])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 236603BromodiphenylmethaneHCID 2521375-Bromo-1H-indole-2-carboxylic acid

생성물 1

HCID 229882391-Benzhydryl-5-bromo-1H-indole-2-carboxylic Acid수율 87.2%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
50 °C

실험 절차

To 5-bromoindole-2-carboxylic acid (1.024 g, 4.26 mmol) in 1-methyl-2-pyrrolidinone (13 mL) at 0° C. were added iPr2NEt (25.6 mmol), tetrabutylammonium iodide (157 mg, 0.426 mmol) and bromodiphenylmethane (1.20 g, 4.86 mmol). The reaction mixture was heated at 50° C. for 21 h before partitioning between diethyl ether and ice water. After adjusting the pH to 3, the aqueous layer was extracted with diethyl ether. The organic layers were combined, washed with NaH2PO4, dried over MgSO4 and evaporated to dryness. Purification on silica gel column (15% EtOAc in hexane) yielded 1.51 g (87% yield) of the product.

후처리

  1. custombefore partitioning between diethyl ether and ice water
  2. extractionthe aqueous layer was extracted with diethyl ether
  3. washwashed with NaH2PO4
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customPurification on silica gel column (15% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-6cb4001a5be84c5788f0ca0ba350875e
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06630496B1

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