Bromotrimethylsilane → HCID 86669013, compound

HRID 2366278Notes

Reaction equation

HRID 2366278 reaction equation
C[Si]([Br:5])(C)C.[Cl:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([Cl:26])[C:14]=1[C:15]1[S:16][C:17]2[C:18](Cl)=[N:19][CH:20]=[C:21]([F:24])[C:22]=2[N:23]=1)[C:10]#[N:11].C([O-])(O)=O.[Na+]>C(#N)CC>[Br:5][C:18]1[C:17]2[S:16][C:15]([C:14]3[C:7]([Cl:6])=[CH:8][C:9]([C:10]#[N:11])=[CH:12][C:13]=3[Cl:26])=[N:23][C:22]=2[C:21]([F:24])=[CH:20][N:19]=1

Participants

5

Reactant 3

HCID 76113BromotrimethylsilaneHCID 516892Sodium BicarbonateHCID 86669014HCID 86669014, compound

Product 1

HCID 86669013HCID 86669013, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Conditions

Temperature
85 °C

Procedure

Trimethylsilyl bromide (0.14 mL, 1.08 mmol) was added to a solution of 3,5-dichloro-4-(4-chloro-7-fluorothiazolo[5,4-c]pyridin-2-yl)-benzonitrile (0.130 g, 0.36 mmol) in propionitrile (3 mL) at room temperature under a nitrogen atmosphere. The reaction mixture was heated at 85° C. for 18 hours then allowed to stand at room temperature for 48 hours. The resultant mixture was poured into an ice-cooled saturated solution of NaHCO3 and extracted with EtOAc (×2). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to afford the title compound as an off-white solid (131 mg, 90% yield). 1H NMR (400 MHz, CDCl3): δ 8.42 (d, J=1.8 Hz, 1H), 7.78 (s, 2H).

Workup

  1. extractionextracted with EtOAc (×2)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-96a89508fce840ffb7a7a034606a6ce1
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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