3,3-Dimethylbutanoyl chloride → HCID 18947572, compound

HRID 327265Notes

Reaction equation

[Cl:1][C:2]1[CH:39]=[CH:38][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)=[CH:13][CH:14]=3)[CH:9]=[C:8]2[CH2:28][C:29]([CH2:36][CH3:37])([CH2:34][CH3:35])[C:30]([O:32][CH3:33])=[O:31])=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:44]([CH2:48][C:49](Cl)=[O:50])([CH3:47])([CH3:46])[CH3:45]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)=[CH:13][CH:14]=3)[C:9]([C:49](=[O:50])[CH2:48][C:44]([CH3:47])([CH3:46])[CH3:45])=[C:8]2[CH2:28][C:29]([CH2:34][CH3:35])([CH2:36][CH3:37])[C:30]([O:32][CH3:33])=[O:31])=[CH:38][CH:39]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold solution (0° C.) of methyl 3-[N-(4-chlorobenzyl)-5-(quinolin-2-ylmethoxy)indol-2-yl]-2,2-diethylpropanoate (from Step D) (177 mg, 0.33 mmol) in CH2Cl2 (3 mL) was added AlCl3 (220 mg, 1.65 mmol) followed by t-butylacetyl chloride (82 μL, 0.66 mmol). The reaction was stirred at 0° C. for 20 minutes and then quenched with 30 mL of 0.5N Na, K tartrate solution, and extracted with 3×30 mL of EtOAc. The organic layers were combined and dried over MgSO4. Filtration and concentration gave an oily residue which was purified by flash chromatography (eluant: EtOAc-hexane 17:83) to give the title compound.

Workup

customquenched with 30 mL of 0.5N Na, K tartrate solution
extractionextracted with 3×30 mL of EtOAc
dry with materialdried over MgSO4
filtrationFiltration and concentration
customgave an oily residue which
customwas purified by flash chromatography (eluant: EtOAc-hexane 17:83)

Sources & evidence

ORD record: ord-da53e91a6266435689d4f61fb3c2c9ea
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05272145

Reaction notes

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