Ethyl acetate hexane → 4-(Dimethylamino)-N-(2-fluoro-3-(1-(6-morpholino-1H-indol-3-yl)-2-nitroethyl)phenyl)benzamide

HRID 2361353Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[CH:8]=2)[CH:3]=[CH:2]1.[CH3:16][N:17]([CH3:39])[C:18]1[CH:38]=[CH:37][C:21]([C:22]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27](/[CH:31]=[CH:32]/[N+:33]([O-:35])=[O:34])[C:26]=2[F:36])=[O:23])=[CH:20][CH:19]=1.FC(F)(F)S(O[Yb](OS(C(F)(F)F)(=O)=O)OS(C(F)(F)F)(=O)=O)(=O)=O.C(OCC)(=O)C.CCCCCC>C(#N)C>[CH3:39][N:17]([CH3:16])[C:18]1[CH:19]=[CH:20][C:21]([C:22]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH:31]([C:3]3[C:4]4[C:9](=[CH:8][C:7]([N:10]5[CH2:15][CH2:14][O:13][CH2:12][CH2:11]5)=[CH:6][CH:5]=4)[NH:1][CH:2]=3)[CH2:32][N+:33]([O-:35])=[O:34])[C:26]=2[F:36])=[O:23])=[CH:37][CH:38]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 4-(1H-indol-6-yl)morpholine (0.393 g, 1.943 mmol), (E)-4-(dimethylamino)-N-(2-fluoro-3-(2-nitrovinyl)phenyl)benzamide (0.400 g, 1.215 mmol), and tris(trifluoromethylsulfonyloxy)ytterbium (0.075 g, 0.121 mmol) in acetonitrile (25 mL) was heated at 50° C. for 20 h. The acetonitrile was removed under vacuum. The residue was diluted with ethyl acetate (180 mL), washed with 10% NaHCO3 solution (2×40 mL) and brine (40 mL), and dried over anhydrous MgSO4. The desired product (0.412 g, 0.750 mmol, 61.8% yield) was isolated with ISCO (80 g silica gel, 30-80% ethyl acetate/hexane) as a pale yellow solid.

Workup

customThe acetonitrile was removed under vacuum
additionThe residue was diluted with ethyl acetate (180 mL)
washwashed with 10% NaHCO3 solution (2×40 mL) and brine (40 mL)
dry with materialdried over anhydrous MgSO4

Sources & evidence

ORD record: ord-ce114c63a058416f97c971405b9d76b9
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685969B2

Reaction notes

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