Ethyl Acetate → 2-(2,6-dimethylphenyl)-1H-indole-6-carboxylic acid (4-tert-butylphenyl)-amide

HRID 1514932

반응식

HRID 1514932 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([C:18](O)=[O:19])[CH:12]=2.[C:21]([C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(OCC)(=O)C>CN(C=O)C>[C:21]([C:25]1[CH:26]=[CH:27][C:28]([NH:29][C:18]([C:13]2[CH:12]=[C:11]3[C:16]([CH:17]=[C:9]([C:3]4[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=4[CH3:1])[NH:10]3)=[CH:15][CH:14]=2)=[O:19])=[CH:30][CH:31]=1)([CH3:24])([CH3:22])[CH3:23]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 698614-Tert-ButylanilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 669653062-(2,6-dimethylphenyl)-1H-indole-6-carboxylic acid

생성물 1

HCID 669656932-(2,6-dimethylphenyl)-1H-indole-6-carboxylic acid (4-tert-butylphenyl)-amide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 2-(2,6-dimethylphenyl)-1H-indole-6-carboxylic acid. (17 mg, 60 μmol), 4-tert.-butylaniline (10 μL, 9.4 mg, 63 μmol) and HATU (33 mg, 87 μmol) in DMF (3 mL) was stirred, initially at ambient temperature, then at 60° C. for 18 h. The mixture was poured into ethyl acetate and extracted once with water and five times with brine. The organic layer was dried, filtered, and solvent was removed under reduced pressure. The residual material was chromatographed using a gradient of 20-60% heptane/ethyl acetate to give 2-(2,6-dimethylphenyl)-1H-indole-6-carboxylic acid (4-tert-butylphenyl)-amide. 1H NMR (CDCl3, 400 MHz) δ 8.54 (s, broad, 1H), 8.12 (s, 1H), 7.89 (s, 1H), 7.70 (d, J=8.3 Hz, 1H), 7.56 (m, 3H), 7.37 (d, J=8.7 Hz, 2H), 7.15 (d, J=7.6 Hz, 2H), 6.46 (s, 1H), 2.18 (s, 6H), 1.33 (s, 9H). MS (m/z) 397.2 (M+1).

후처리

  1. extractionextracted once with water and five times with brine
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. customsolvent was removed under reduced pressure
  5. customThe residual material was chromatographed

출처 및 근거

ORD 기록
ord-cacfd5e814e447daabc192fc744299d2
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222248B2

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