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

HRID 1014284ノート

反応式

HRID 1014284 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 21939870Tetrahydrofuran ethyl acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-75e4a29d7e704436bb9e0c616f0a76ef
出典データセット
uspto-grants-2011_07
特許番号
US07981903B2

反応ノート

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