Triphenylphosphine → 5-(12-fluoro-6,7-dihydro-5H-pyrido[2',3':3,4]azepino[1,2-a]indol-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

HRID 595742

Reaktionsgleichung

Reaktionsgleichung von HRID 595742
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]1[N:16]=[C:15]([C:17]3[C:18]([N:37]([CH3:42])[S:38]([CH3:41])(=[O:40])=[O:39])=[CH:19][C:20]4[O:24][C:23]([C:25]5[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=5)=[C:22]([C:32]([NH:34][CH3:35])=[O:33])[C:21]=4[CH:36]=3)[CH:14]=[CH:13][C:12]=1[CH2:43][CH2:44][CH2:45]O)[NH:6]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[F:1][C:2]1[C:3]2[CH:4]=[C:5]3[C:11]4[N:16]=[C:15]([C:17]5[C:18]([N:37]([CH3:42])[S:38]([CH3:41])(=[O:39])=[O:40])=[CH:19][C:20]6[O:24][C:23]([C:25]7[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=7)=[C:22]([C:32]([NH:34][CH3:35])=[O:33])[C:21]=6[CH:36]=5)[CH:14]=[CH:13][C:12]=4[CH2:43][CH2:44][CH2:45][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 903336015-(6-(4-fluoro-1H-indol-2-yl)-5-(3-hydroxypropyl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Produkt 1

HCID 903338445-(12-fluoro-6,7-dihydro-5H-pyrido[2',3':3,4]azepino[1,2-a]indol-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-(6-(4-fluoro-1H-indol-2-yl)-5-(3-hydroxypropyl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (153 mg, 0.237 mmol) and triphenylphosphine (62.2 mg, 0.237 mmol) in THF was added diisopropyl azodicarboxylate (0.046 mL, 0.237 mmol). The resultant mixture was stirred at ambient temperature for 10 h then was concentrated in vacuo and the residue purified by silica gel column chromatography using a step gradient of 0-50-100% EtOAc/Hexanes as eluent. 1H NMR δ (ppm) (CHCl3-d): 8.07 (1H, s), 8.02 (2H, dd, J=8.61, 5.32 Hz), 7.75 (1H, d, J=7.78 Hz), 7.70 (1H, s), 7.60 (1H, d, J=7.77 Hz), 7.26˜7.0 (4H, m), 7.09 (1H, s), 6.85˜6.81 (1H, m), 5.98 (1H, br s), 4.23 (2H, t, J=6.66 Hz), 3.35 (3H, s), 3.03 (3H, d, J=4.90 Hz), 2.85 (2H, t, J=7.00 Hz), 2.80 (3H, s), 2.47˜2.42 (2H, m), MS (M+H)+: 627.

Aufarbeitung

  1. concentrationthen was concentrated in vacuo
  2. customthe residue purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e3fb3e3b5efb42868e1d52b44f02c8d4
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09243002B2

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