Acetonitrile → HCID 90418212, compound

HRID 923692Notes

Reaction equation

[NH2:1][C:2]1[C:7]([F:8])=[C:6](Br)[N:5]=[C:4]([C:10]([O:12][CH3:13])=[O:11])[C:3]=1[Cl:14].[S:15]1[C:19]2[CH:20]=[CH:21][C:22](B(O)O)=[CH:23][C:18]=2[N:17]=[CH:16]1.[F-].[K+].CC#N>ClCCl.CC([O-])=O.CC([O-])=O.[Pd+2].O>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:22]2[CH:21]=[CH:20][C:19]3[S:15][CH:16]=[N:17][C:18]=3[CH:23]=2)[N:5]=[C:4]([C:10]([O:12][CH3:13])=[O:11])[C:3]=1[Cl:14]

Participants

Conditions

Temperature: 150 °C

Procedure

To a 5 mL microwave vial was added methyl 4-amino-6-bromo-3-chloro-5-fluoropicolinate (200 mg, 1.0 mmol), benzo[d]thiazol-5-ylboronic acid (237 mg, 1.35 mmol), potassium fluoride (KF; 122 mg, 2.12 mmol), TPPTS-Na (tris-(3-sulfornatophenyl)-phosphine4-hydrate sodium salt, 67 mg, 0.106 mmol) and Pd(OAc)2 (11 mg, 0.053 mmol). Subsequently, CH3CN (1.0 mL) and H2O (3.0 mL) were added, and the reaction vial was sealed and heated in a Biotage microwave at 150° C. for 5 min, with external IR-sensor temperature monitoring from the side of the vessel. The reaction mixture was cooled to room temperature and diluted with dicloromethane, and washed wth water. The organic extracts were combined, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by triturating with Et2O to yield the title compound as a brown solid (172 mg, 51%).

Workup

customthe reaction
customvial was sealed
temperatureThe reaction mixture was cooled to room temperature
washwashed wth water
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude product was purified
customby triturating with Et2O

Sources & evidence

ORD record: ord-dafc6c759c97436dba1f3cf3e64c8984
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278985B2

Reaction notes

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