Acetamide → HCID 58505552, compound

HRID 1917618Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([C:9]([C:11]2[N:19]3[C:14]([CH:15]=[C:16]([CH:20]([CH3:22])[CH3:21])[CH:17]=[CH:18]3)=[C:13]([C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[C:12]=2[CH2:29][C:30]([CH3:36])([CH3:35])[C:31]([O:33][CH3:34])=[O:32])=[O:10])[CH:6]=[CH:7][CH:8]=1)#[N:2].C(N)(=[O:39])C>C1COCC1.O.[Pd](Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([C:9]([C:11]2[N:19]3[C:14]([CH:15]=[C:16]([CH:20]([CH3:22])[CH3:21])[CH:17]=[CH:18]3)=[C:13]([C:23](=[O:28])[C:24]([CH3:25])([CH3:26])[CH3:27])[C:12]=2[CH2:29][C:30]([CH3:36])([CH3:35])[C:31]([O:33][CH3:34])=[O:32])=[O:10])[CH:6]=[CH:7][CH:8]=1)(=[O:39])[NH2:2]

Participants

Conditions

Temperature: 23 °C

Procedure

A solution of methyl 3-{3-[(3-cyanophenyl)carbonyl]-1-(2,2-dimethylpropanoyl)-7-(propan-2-yl)indolizin-2-yl}-2,2-dimethylpropanoate (125 mg, 0.257 mmol), palladium(II) chloride (9.1 mg, 0.051 mmol), and acetamide (152 mg, 2.57 mmol) in THF (1.5 mL) and water (0.5 mL) is heated at 50° C. for 3 h then cooled to 23° C. and partitioned between water and Et2O. The organics are washed with water, dried with MgSO4, filtered, and concentrated in vacuo. Purification of the crude by flash chromatography (SiO2, hexanes to 75% EtOAc in hexanes) gives methyl 3-{3-[(3-carbamoylphenyl)carbonyl]-1-(2,2-dimethylpropanoyl)-7-(propan-2-yl)indolizin-2-yl}-2,2-dimethylpropanoate (114 mg, 88%).

Workup

custompartitioned between water and Et2O
washThe organics are washed with water
dry with materialdried with MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurification of the crude by flash chromatography (SiO2, hexanes to 75% EtOAc in hexanes)

Sources & evidence

ORD record: ord-9c5420cc13954c348a5a582fc391153e
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618300B2

Reaction notes

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