Potassium Carbonate → HCID 58505759, compound

HRID 1917605Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[N:18]3[C:13]([CH:14]=[C:15]([OH:19])[CH:16]=[CH:17]3)=[C:12]([C:20](=[O:26])[CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:11]=2[CH2:27][C:28]([CH3:35])([CH3:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:9])=[CH:4][CH:3]=1.Br[CH2:37][C:38]1[CH:47]=[CH:46][C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[N:39]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[N:18]3[C:13]([CH:14]=[C:15]([O:19][CH2:37][C:38]4[CH:47]=[CH:46][C:45]5[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=5)[N:39]=4)[CH:16]=[CH:17]3)=[C:12]([C:20](=[O:26])[CH2:21][C:22]([CH3:23])([CH3:24])[CH3:25])[C:11]=2[CH2:27][C:28]([CH3:34])([CH3:35])[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:9])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of ethyl 3-{3-[(4-chlorophenyl)carbonyl]-1-(3,3-dimethylbutanoyl)-7-hydroxyindolizin-2-yl}-2,2-dimethylpropanoate (30 mg, 0.06 mmol), 2-(bromomethyl)quinoline (20 mg, 0.09 mmol), and potassium carbonate (17 mg, 0.12 mmol) in DMF (1.0 mL) is stirred for 96 h at 50° C. The mixture is cooled to 23° C. then filtered and concentrated in vacuo. Purification of the crude by flash chromatography (SiO2, hexanes to 1:1 hexanes:EtOAc) gives ethyl 3-{3-[(4-chlorophenyl)carbonyl]-1-(3,3-dimethylbutanoyl)-7-(quinolin-2-ylmethoxy)indolizin-2-yl}-2,2-dimethylpropanoate (39 mg, quant).

Workup

temperatureThe mixture is cooled to 23° C.
filtrationthen filtered
concentrationconcentrated in vacuo
customPurification of the crude by flash chromatography (SiO2, hexanes to 1:1 hexanes:EtOAc)

Sources & evidence

ORD record: ord-db5fa192280f450bb18380597a15dbd2
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618300B2

Reaction notes

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