Pyridine → 3-Chloro-3-(2-ethoxy-phenyl)-5-methoxy-1,3-dihydro-indol-2-one

HRID 2040438Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1(O)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=2)[NH:12][C:11]1=[O:21])[CH3:2].N1C=CC=CC=1.O=S(Cl)[Cl:31]>C(Cl)Cl>[Cl:31][C:10]1([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[O:3][CH2:1][CH3:2])[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=2)[NH:12][C:11]1=[O:21]

Participants

Conditions

Temperature: 0 °C

Procedure

5 g (16.7 mmol) of the intermediate from Step A and 2.6 g (33.4 mmol) pyridine were dissolved in 50 mL CH2Cl2 and at 0° C. 3 g (25.1 mmol) SOCl2 were added slowly. Then the reaction mixture was stirred for 30 min. at 0° C. The reaction mixture was poured into an ice/water mixture and the organic phase was separated, washed with H2O, dried over magnesium sulfate and finally the solvent was removed in vacuo. The resulting residue was suspended in ether. The solid residue was separated and dried to give 3.2 g of the intermediate, which was used without further purification.

Workup

customthe organic phase was separated
washwashed with H2O
dry with materialdried over magnesium sulfate
customfinally the solvent was removed in vacuo
customThe solid residue was separated
customdried

Sources & evidence

ORD record: ord-4b561c9fc5af48d381bbd4a99775152a
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580842B2

Reaction notes

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