Potassium Carbonate → HCID 86669011, compound

HRID 2366271Notes

Reaction equation

HRID 2366271 reaction equation
C[Si]([Br:5])(C)C.Cl[C:7]1[C:12]2[S:13][C:14]([C:16]3[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:23])=[N:15][C:11]=2[C:10]([F:24])=[CH:9][N:8]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)CC>[Br:5][C:7]1[C:12]2[S:13][C:14]([C:16]3[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:23])=[N:15][C:11]=2[C:10]([F:24])=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76113BromotrimethylsilaneHCID 86669012HCID 86669012, compound

Product 1

HCID 86669011HCID 86669011, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Conditions

Temperature
85 °C

Procedure

Trimethylsilyl bromide (1.2 mL, 9.0 mmol) was added to a solution of 4-chloro-2-(2,6-dichlorophenyl)-7-fluorothiazolo[5,4-c]pyridine (1.0 g, 3.0 mmol) in propionitrile (30 mL) at room temperature under argon. The reaction mixture was heated at 85° C. in a sealed vial for 16 hours. The resultant mixture was poured in an ice-cooled saturated solution of potassium carbonate. The product was extracted with DCM (×2) and the combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to afford the title compound as an off-white solid (1.17 g, quantitative). LCMS (Method E): RT=4.32 min, m/z: 379 [M+H+].

Workup

  1. extractionThe product was extracted with DCM (×2)
  2. dry with materialthe combined organic layers were dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-59cc1d4bbde1465ea8c9d6507f9de930
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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