Bromotrimethylsilane → HCID 86669020, compound

HRID 2366292Notes

Reaction equation

HRID 2366292 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]=[C:21]([F:24])[C:22]=3[N:23]=2)=[C:9]([CH:12]=[CH:13][CH:14]=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:8]3[C:7]([Cl:6])=[CH:14][CH:13]=[CH:12][C:9]=3[C:10]#[N:11])=[N:23][C:22]=2[C:21]([F:24])=[CH:20][N:19]=1

Participants

5

Reactant 3

HCID 76113BromotrimethylsilaneHCID 516892Sodium BicarbonateHCID 86669021HCID 86669021, compound

Product 1

HCID 86669020HCID 86669020, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Conditions

Temperature
50 °C

Procedure

Trimethylsilyl bromide (1.8 mL, 13.2 mmol) was added to a suspension of 3-chloro-2-(4-chloro-7-fluorothiazolo[5,4-c]pyridin-2-yl)-benzonitrile (1.43 g, 4.40 mmol) in propionitrile (40 mL) at room temperature, under argon. The reaction mixture was heated at 50° C. for 7 hours. The reaction mixture was adjusted to pH 7 by careful addition of a saturated aqueous solution of sodium bicarbonate. The resultant mixture was extracted with DCM (×3) and the combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to afford the title compound as an off-white solid (1.65 g, 100% yield). 1H NMR (300 MHz, CDCl3): δ 8.42 (d, J=1.8 Hz, 1H), 7.86-7.79 (m, 2H), 7.66 (t, J=8.0 Hz, 1H).

Workup

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

Sources & evidence

ORD record
ord-24e800f288f942c383c7497d0038f91f
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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