Potassium Carbonate → HCID 86669007, compound

HRID 2366262Notes

Reaction equation

HRID 2366262 reaction equation
C[Si]([Br:5])(C)C.Cl[C:7]1[C:12]2[S:13][C:14]([C:16]3[C:21]([F: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]([F: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 86669008HCID 86669008, compound

Product 1

HCID 86669007HCID 86669007, compoundYield 33.6%

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Conditions

Temperature
85 °C

Procedure

Trimethylsilyl bromide (0.4 mL, 3 mmol) was added to a solution of 4-chloro-2-(2-chloro-6-fluorophenyl)-7-fluorothiazolo[5,4-c]pyridine (0.317 g, 10 mmol) in propionitrile (10 mL) at room temperature under an argon atmosphere. The reaction mixture was heated at 85° C. in a sealed vial for three days then it was poured in an ice-cooled saturated solution of potassium carbonate. The resultant mixture was extracted with DCM (×2). The combined organic washings were dried (Na2SO4) and concentrated under reduced pressure to afford the title compound as an off-white solid (0.365 g, quantitative). 1H NMR (400 MHz, CDCl3): δ 8.39 (d, J=1.9 Hz, 1H), 7.51 (td, J=8.3, 5.8 Hz, 1H), 7.41 (dt, J=8.2, 1.1 Hz, 1H), 7.25-7.16 (m, 1H).

Workup

  1. extractionThe resultant mixture was extracted with DCM (×2)
  2. dry with materialThe combined organic washings were dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7657710849854465a9fd2e09136545fc
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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