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

HRID 987164

反応式

HRID 987164 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6cb4001a5be84c5788f0ca0ba350875e
出典データセット
uspto-grants-2003_10
特許番号
US06630496B1

関連ノート

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