Bromotrimethylsilane → HCID 86723321, compound

HRID 2366283Notes

Reaction equation

HRID 2366283 reaction equation
C[Si]([Br:5])(C)C.[Cl:6][C:7]1[C:8]([C:15]2[S:16][C:17]3[C:18](Cl)=[N:19][CH:20]=[CH:21][C:22]=3[N:23]=2)=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#[N:11]>C(#N)CC>[Br:5][C:18]1[C:17]2[S:16][C:15]([C:8]3[C:7]([Cl:6])=[CH:14][CH:13]=[CH:12][C:9]=3[C:10]#[N:11])=[N:23][C:22]=2[CH:21]=[CH:20][N:19]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 75409785HCID 75409785, compound

Product 1

HCID 86723321HCID 86723321, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Conditions

Temperature
85 °C

Procedure

Trimethylsilyl bromide (1 mL) was added to a solution of 3-chloro-2-(4-chlorothiazolo[5,4-c]pyridine-2-yl)-benzonitrile (0.364 g, 1.18 mmol) in propionitrile (15 mL) at room temperature under a nitrogen atmosphere. The reaction mixture was heated at 85° C. for 2 hours and then the volatiles were removed under reduced pressure. The resultant residue was purified by column chromatography on silica gel eluting with 0-100% methanol in DCM to afford the title compound as a pale brown solid (230 mg, 56% yield). LCMS (Method D): RT=3.70 min, m/z: 337 [M+H+].

Workup

  1. customthe volatiles were removed under reduced pressure
  2. customThe resultant residue was purified by column chromatography on silica gel eluting with 0-100% methanol in DCM

Sources & evidence

ORD record
ord-2c794b4693ba48cb88fd86c8ab045056
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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