Sodium Carbonate → Methyl-2-(3-fluoro-2-methyl-benzyl)-1-phenyl-indolizine-7-carboxylate

HRID 1963053Notes

Reaction equation

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

Participants

Conditions

Temperature: 105 °C

Procedure

The compound of step 1 (1.555 g, 6.84 mmol) and the compound of example 1, step 2 (1.677 g, 6.84 mmol) were dissolved in 28.5 ml of acetone and the solution was heated to reflux overnight. The mixture was then evaporated to dryness under reduced pressure and the residue dissolved in 28.5 ml of isopropanol. Sodium carbonate (2.176 g, 20.53 mmol) was added and the mixture was heated at 105° C. with stirring for 2 h. The solids were filtered off and the filtrate was evaporated to dryness under reduced pressure. The residue was purified by chromatography on silica gel (cyclohexane/EA, 100:0, then 95:5) to give 0.497 g of the title compound as a yellow solid melting at 55° C.

Workup

temperaturethe solution was heated
temperatureto reflux overnight
customThe mixture was then evaporated to dryness under reduced pressure
dissolutionthe residue dissolved in 28.5 ml of isopropanol
filtrationThe solids were filtered off
customthe filtrate was evaporated to dryness under reduced pressure
customThe residue was purified by chromatography on silica gel (cyclohexane/EA, 100:0

Sources & evidence

ORD record: ord-964de9137b6c4c20a8b2cc2ba2995a41
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415336B2

Reaction notes

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