Phenyl chloroformate → [3-(2-Ethoxy-phenyl)-5-methoxy-2-oxo-2,3-dihydro-1H-indol-3-yl]-carbamic acid phenyl ester

HRID 2040440Notes

Reaction equation

[NH2:1][C:2]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH2:21][CH3:22])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH3:12])[CH:9]=2)[NH:4][C:3]1=[O:13].Cl[C:24]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:25]>N1C=CC=CC=1>[C:27]1([O:26][C:24](=[O:25])[NH:1][C:2]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH2:21][CH3:22])[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH3:12])[CH:9]=3)[NH:4][C:3]2=[O:13])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1.8 g (6 mmol) of the intermediate from Step C were dissolved in 20 ml pyridine. At 0° C. 0.99 g (6.3 mmol) phenyl chloroformate were added and afterwards the reaction mixture was stirred for 1 h at 0° C. This mixture was poured into an ice/water mixture. The pH of the aqueous phase was adjusted to 5 and the resulting mixture was extracted with ethyl acetate. The organic phase was separated, dried over magnesium sulfate and the solvent was removed in vacuo. The resulting solid (2 g) was used in the next step without further purification.

Workup

customAt 0° C
extractionthe resulting mixture was extracted with ethyl acetate
customThe organic phase was separated
dry with materialdried over magnesium sulfate
customthe solvent was removed in vacuo
customThe resulting solid (2 g) was used in the next step without further purification

Sources & evidence

ORD record: ord-f5286ad1a4b04177a50c4db7da53279d
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580842B2

Reaction notes

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