Diisopropylethylamine → 8-[[3-(5-fluoro-1H-indol-3-yl)propyl](methyl)amino]-2,3,8,9-tetrahydropyrano[3,2-e]isoindol-1(7H)-one

HRID 1727388Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][CH2:13][NH:14][CH:15]1[CH2:27][O:26][C:25]2[CH:24]=[CH:23][C:22]3[CH2:21][NH:20][C:19](=[O:28])[C:18]=3[C:17]=2[CH2:16]1.[CH3:29]CN(C(C)C)C(C)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][CH2:13][N:14]([CH3:29])[CH:15]1[CH2:27][O:26][C:25]2[CH:24]=[CH:23][C:22]3[CH2:21][NH:20][C:19](=[O:28])[C:18]=3[C:17]=2[CH2:16]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of (3) (52 mg, 0.137 mmol) and Me3OBF4 (40 mg, 0.274 mmol) in methylene chloride (5 ml) was added Hunig's base (40 μl, 0.274 mmol). The reaction mixture was stirred at 50° C. for 2 hr, then diluted with 100 ml of methylene chloride. It was washed with H2O, saturated NaCl. The organic solution was dried over Na2SO4 and concentrated in vacuo. The residue was purified on silica gel eluting with (80% EtOAc/Hexane) to give the title compound, which was treated with 1 equivalent of etherate HCl to give HCl salt. MS (ES) m/z 394.1.

Workup

washIt was washed with H2O, saturated NaCl
dry with materialThe organic solution was dried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified on silica gel eluting with (80% EtOAc/Hexane)

Sources & evidence

ORD record: ord-de5452f6fd70452b9de82a393a1c9ade
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495111B2

Reaction notes

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