Bromotrimethylsilane → HCID 86669033, compound

HRID 2366325Notes

Reaction equation

HRID 2366325 reaction equation
[Cl:1][C:2]1[C:3]([C:11]2[S:12][C:13]3[C:14](Cl)=[N:15][CH:16]=[CH:17][C:18]=3[N:19]=2)=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[C:5]#[N:6].[Br:21][Si](C)(C)C.C(=O)(O)[O-].[Na+]>C(#N)CC>[Br:21][C:14]1[C:13]2[S:12][C:11]([C:3]3[C:2]([Cl:1])=[CH:9][C:8]([F:10])=[CH:7][C:4]=3[C:5]#[N:6])=[N:19][C:18]=2[CH:17]=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 76113BromotrimethylsilaneHCID 516892Sodium BicarbonateHCID 86669034HCID 86669034, compound

Product 1

HCID 86669033HCID 86669033, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 3-chloro-2-(4-chlorothiazolo[5,4-c]pyridin-2-yl)-5-fluorobenzonitrile (118 mg, 0.36 mmol) in propionitrile (3.5 mL) was added bromotrimethylsilane (0.15 mL, 1.1 mmol) and the reaction mixture was heated at 50° C. for 7 hours. The cooled mixture was treated with aqueous sodium bicarbonate and extracted three times with DCM. The combined organic washings were dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a yellow solid (133 mg, 100%). 1H NMR (300 MHz, CDCl3): δ 8.53 (d, J=5.6 Hz, 1H), 8.04 (d, J=5.6 Hz, 1H), 7.59 (dd, J=7.7, 2.5 Hz, 1H), 7.55 (dd, J=7.3, 2.5 Hz, 1H). LCMS (Method D): RT=3.88, m/z: 368 [M+H+].

Workup

  1. extractionextracted three times with DCM
  2. dry with materialThe combined organic washings were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-868d1e2d6e1f47cc92ed457859244465
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

Loading…