Bromotrimethylsilane → HCID 86669023, compound

HRID 2366298Notes

Reaction equation

HRID 2366298 reaction equation
C[Si]([Br:5])(C)C.[F: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]([F: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 86669024HCID 86669024, compound

Product 1

HCID 86669023HCID 86669023, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Conditions

Temperature
50 °C

Procedure

Trimethylsilyl bromide (0.92 mL, 6.85 mmol) was added to a suspension of 3-fluoro-2-(4-chloro-7-fluorothiazolo[5,4-c]pyridin-2-yl)-benzonitrile (0.70 g, 2.28 mmol) in propionitrile (20 mL) at room temperature, under argon. The reaction mixture was heated at 50° C. for 16 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. The resultant solid was triturated with diethyl ether and dried under vacuum to afford the title compound as an off-white solid (0.76 g, 95% yield). LCMS (Method D): RT=3.87 min, m/z: 352 [M+H+].

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
  4. customThe resultant solid was triturated with diethyl ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-2c22bdb375d34db9af7a74cc805aecd8
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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