Methanol → HCID 86648961, compound

HRID 449921Notes

Reaction equation

[Cl:1][C:2]1[CH:22]=[C:21]([CH:23]=C)[CH:20]=[C:19]([Cl:25])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([CH:16]2[CH2:18][CH2:17]2)=[O:15])[CH:8]=1)=[O:5].C[OH:27]>C(Cl)Cl>[Cl:25][C:19]1[CH:20]=[C:21]([CH:23]=[O:27])[CH:22]=[C:2]([Cl:1])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([CH:16]2[CH2:17][CH2:18]2)=[O:15])[CH:8]=1)=[O:5]

Participants

Conditions

Temperature: -78 °C

Procedure

2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)-4-vinylbenzamide (750 mg, 1.99 mmol) was dissolved in a solution of MeOH (14 mL) and DCM (28 mL). The resulting mixture was cooled to −78° C., O3 was bubbled into the solution for 7 min, N2 was bubbled for 10 min, and then Me2S (14 mL) was added. The reaction mixture was slowly warmed to room temperature and stirred for 20 min. The mixture was concentrated under reduced pressure to provide 2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)-4-formylbenzamide (0.70 g, yield: 86%). LCMS (ESI) m/z: 378.1 [M+H+].

Workup

customO3 was bubbled into the solution for 7 min
customN2 was bubbled for 10 min
additionMe2S (14 mL) was added
temperatureThe reaction mixture was slowly warmed to room temperature
concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-0aff287a4b6d4fa2a0cca6e23d01d417
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486950B2

Reaction notes

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