Cesium carbonate → HCID 57552218, compound

HRID 1986898Notes

Reaction equation

[CH2:1]([N:8]1[C:25]([CH3:26])=[C:11]2[C:12](=[O:24])[NH:13][C:14]3[CH:15]=[C:16]4[CH2:23][CH2:22][CH2:21][CH2:20][C:17]4=[CH:18][C:19]=3[C:10]2=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:34][CH:35]([F:45])[CH2:36][NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41]>CN(C=O)C>[CH2:1]([N:8]1[C:25]([CH3:26])=[C:11]2[C:12](=[O:24])[N:13]([CH2:34][CH:35]([F:45])[CH2:36][NH:37][C:38](=[O:44])[O:39][C:40]([CH3:42])([CH3:41])[CH3:43])[C:14]3[CH:15]=[C:16]4[CH2:23][CH2:22][CH2:21][CH2:20][C:17]4=[CH:18][C:19]=3[C:10]2=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a mixture of 2-benzyl-3-methyl-2,5,7,8,9,10-hexahydro-4H-benzo[g]pyrazolo[4,3-c]quinolin-4-one (1-7) (8.0 g, 23 mmol, 1 equiv) and cesium carbonate (37 g, 110 mmol, 4.9 equiv) in DMF (100 mL) was added tert-butyl 3-bromo-2-fluoropropylcarbamate (1-9) (7.1 g, 27.7 mmol, 1.2 equiv) and the resulting mixture was stirred at 40° C. for 16 h. The reaction mixture was filtered and the filtrate concentrated and purified by silica gel chromatography (100% hexanes to 100% ethyl acetate over 1 h) to yield tert-butyl 3-(2-benzyl-3-methyl-4-oxo-2,4,7,8,9,10-hexahydro-5H-benzo[g]pyrazolo[4,3-c]quinolin-5-yl)-2-fluoropropylcarbamate (1-10) as a white solid. LRMS m/z (M+H) 519.2 found, 519.3 required.

Workup

filtrationThe reaction mixture was filtered
concentrationthe filtrate concentrated
custompurified by silica gel chromatography (100% hexanes to 100% ethyl acetate over 1 h)

Sources & evidence

ORD record: ord-884a37633f354c1da3ad2c7724742451
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07550477B2

Reaction notes

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