Potassium Carbonate → HCID 68510552, compound

HRID 1810096Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

To a mixture of tert-butyl 2-(3-cyano-4-fluorophenyl)acetate (0.150 g, 0.6376 mmol) and N-(4-chlorophenethyl)-1H-indole-5carboxamide (0.2095 g, 0.7014 mmol) in DMSO (3 mL) was added K2CO3 (0.1322 g, 0.9564 mmol), and the reaction mixture was heated at 120° C. for 30 minutes, then at 130° C. for 1 hour. The reaction was diluted with ethyl acetate and the organic layer was washed with water and brine, dried over magnesium sulfate and concentrated. The residue was purified by silica gel chromatography eluting with a gradient of 5% to 100% ethyl acetate/hexanes to provide tert-butyl 2-(4-(5-((4-chlorophenethyl)carbamoyl)-1H-indol-1-yl)-3cyanophenyl)acetate (0.160 g, 48.82% yield) as a waxy solid. MS (APCI)=514.0 (M+1).

Workup

washthe organic layer was washed with water and brine
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe residue was purified by silica gel chromatography
washeluting with a gradient of 5% to 100% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-339b430e8337425e8f1492408092213f
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362056B2

Reaction notes

Loading…