N-Iodosuccinimide → 7-Iodo-2-methyl-5H-thiazolo[4,5-c]pyridin-4-one

HRID 1443114Notes

Reaction equation

[CH3:1][C:2]1[S:3][C:4]2[CH:9]=[CH:8][NH:7][C:6](=[O:10])[C:5]=2[N:11]=1.[I:12]N1C(=O)CCC1=O>C(#N)C>[I:12][C:9]1[C:4]2[S:3][C:2]([CH3:1])=[N:11][C:5]=2[C:6](=[O:10])[NH:7][CH:8]=1

Participants

Conditions

Temperature: 5 °C

Procedure

2-Methyl-5H-thiazolo[4,5-c]pyridin-4-one (770 mg, 4.6 mmol) was suspended in 25 ml acetonitrile and N-iodosuccinimide (1.04 g, 4.6 mmol) was added. The reaction mixture was refluxed for 3 hrs. The brown suspension was cooled to 5° C. and stirred for 15 min. The solid was filtered, washed with cold acetonitrile and dried for 1 hour at 50° C. and <30 mbar. The crude product (830 mg, 61%) [MS: m/e=292.9 (M+H+)] was used without any further purification for the next step.

Workup

temperatureThe reaction mixture was refluxed for 3 hrs
filtrationThe solid was filtered
washwashed with cold acetonitrile
customdried for 1 hour at 50° C.
customThe crude product (830 mg, 61%) [MS: m/e=292.9 (M+H+)] was used without any further purification for the next step

Sources & evidence

ORD record: ord-ab41380a4b9b4e1cb3eca0d41b2332df
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07659401B2

Reaction notes

Loading…