Diisopropylethylamine → 5-(methyloxy)-1-(1-methyl-L-prolyl)-6-nitro-2,3-dihydro-1H-indole

HRID 1014284노트

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HRID 1014284 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[NH:8][CH2:7][CH2:6]2.[CH3:15][N:16]1[CH2:23][CH2:22][CH2:21][C@H:17]1[C:18](O)=[O:19].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C)C=O.C(OCC)(=O)C.C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[N:8]([C:18](=[O:19])[C@@H:17]1[CH2:21][CH2:22][CH2:23][N:16]1[CH3:15])[CH2:7][CH2:6]2

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 643474N-Methyl-L-prolineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 594416565-methoxy-6-nitro-2,3-dihydro-1H-indole

생성물 1

HCID 673158805-(methyloxy)-1-(1-methyl-L-prolyl)-6-nitro-2,3-dihydro-1H-indole수율 95.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 21939870Tetrahydrofuran ethyl acetate용매

실험 절차

A solution of 5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole (2.7 g, 11.71 mmol), 1-methyl-L-proline (Acros, 1.739 g, 13.46 mmol), HATU (5.79 g, 15.22 mmol), and DIPEA (6.13 mL, 35.1 mmol) in N,N-Dimethylformamide (DMF) (25 mL) was stirred at room temperature overnight. The next morning the solution had completely solidified. The solids were diluted with ethyl acetate/THF and washed with saturated sodium bicarbonate until all solids had dissolved. The organic layer was dried over sodium sulfate, filtered, concentrated onto celite, and purified by column chromatography to afford 5-(methyloxy)-1-(1-methyl-L-prolyl)-6-nitro-2,3-dihydro-1H-indole (3.4 g, 95% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.51 (s, 1 H), 7.35 (s, 1 H), 4.20-4.31 (m, 1 H), 4.10-4.20 (m, 1 H), 3.88 (s, 3 H), 3.56-3.70 (m, 1 H), 3.25 (t, J=8.43 Hz, 2 H), 3.15-3.21 (m, 1 H), 2.52-.64 (m, 1H), 2.45 (s, 3 H), 2.21-2.35 (m, 1 H), 1.75-1.93 (m, 3 H).

후처리

  1. washwashed with saturated sodium bicarbonate until all solids
  2. dissolutionhad dissolved
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated onto celite
  6. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-75e4a29d7e704436bb9e0c616f0a76ef
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

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