1,2-Dichloroethane → 5-[(1H-Indol-4-ylmethyl)-carbamoyl]-3-trifluoromethyl-thiophene-2-carboxylic acid methyl ester

HRID 1952577노트

반응식

HRID 1952577 반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:14]([OH:16])=O)=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])=[O:4].C(N(CC)CC)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH:38]1[C:46]2[C:41](=[C:42]([CH2:47][NH2:48])[CH:43]=[CH:44][CH:45]=2)[CH:40]=[CH:39]1>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:14](=[O:16])[NH:48][CH2:47][C:42]2[CH:43]=[CH:44][CH:45]=[C:46]3[C:41]=2[CH:40]=[CH:39][NH:38]3)=[CH:8][C:9]=1[C:10]([F:11])([F:12])[F:13])=[O:4]

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 280302(1H-indol-4-yl)methanamineHCID 682266025-(Methoxycarbonyl)-4-(trifluoromethyl)thiophene-2-carboxylic acid

생성물 1

HCID 682269315-[(1H-Indol-4-ylmethyl)-carbamoyl]-3-trifluoromethyl-thiophene-2-carboxylic acid methyl ester수율 31.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-Trifluoromethyl-thiophene-2,5-dicarboxylic acid 2-methyl ester (570 mg, 2.24 mmol) in anhydrous DMF (10 mL) was added triethylamine (1.25 mL, 8.96 mmol), EDC (520 mg, 2.69 mmol), HOBT (360 mg, 2.69 mmol), and C-(1H-Indol-4-yl)-methylamine (390 mg, 2.69 mmol). The mixture was stirred at room temperature 3 h, then quenched by pouring into EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography with 0-70% EtOAc in hexane to afford the desired product (0.27 g, 31% yield).

후처리

  1. customquenched
  2. additionby pouring into EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography with 0-70% EtOAc in hexane

출처 및 근거

ORD 기록
ord-e1ca80035e7748fbbae440ed41d9c92f
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404859B2

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