Pyridine → 4-Chloro-2-(2,6-dichloro-4-iodophenyl)thiazolo[5,4-c]pyridine

HRID 2366220Notes

Reaction equation

[Cl:1][C:2]1[CH:18]=[C:17]([I:19])[CH:16]=[C:15]([Cl:20])[C:3]=1[C:4](Cl)=[N:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([Cl:12])[C:7]=1F.NC(N)=[S:23].N1C=CC=CC=1.C(N(CC)CC)C>C(O)(C)C>[Cl:12][C:8]1[C:7]2[S:23][C:4]([C:3]3[C:2]([Cl:1])=[CH:18][C:17]([I:19])=[CH:16][C:15]=3[Cl:20])=[N:5][C:6]=2[CH:11]=[CH:10][N:9]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 2,6-dichloro-N-(2-chloro-3-fluoropyridin-4-yl)-4-iodobenzimidoyl chloride (2.94 g, 6.30 mmol), thiourea (1.93 g, 25.3 mmol) and pyridine (1.73 mL, 21.4 mmol) in isopropanol (25 mL) was heated to 90° C. for 3.5 hours. Triethylamine (5.3 mL, 37.8 mmol) was added and the resulting mixture was heated to 90° C. for a further 1.5 h. The reaction was cooled to room temperature and then concentrated under reduced pressure. The resultant residue was partitioned between DCM and water. The organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure. The residue was triturated with MeOH and dried under reduced pressure to give the desired compound (2.33 g, 84% yield). 1H NMR (300 MHz, CDCl3): δ 8.52 (d, J=5.6 Hz, 1H), 7.98 (d, J=5.6 Hz, 1H), 7.90-7.81 (s, 2H).

Workup

temperaturethe resulting mixture was heated to 90° C. for a further 1.5 h
temperatureThe reaction was cooled to room temperature
concentrationconcentrated under reduced pressure
customThe resultant residue was partitioned between DCM and water
customThe organic layer was separated
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customThe residue was triturated with MeOH
customdried under reduced pressure

Sources & evidence

ORD record: ord-59b698bf1f0c4408ba770ba0f95c2f48
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697708B2

Reaction notes

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