Dichloromethane → 4-(4-Bromothiazolo[5,4-c]pyridin-2-yl)-3,5-dichlorobenzonitrile

HRID 2366212Notes

Reaction equation

HRID 2366212 reaction equation
C[Si]([Br:5])(C)C.[Cl:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([Cl:25])[C:14]=1[C:15]1[S:16][C:17]2[C:18](Cl)=[N:19][CH:20]=[CH:21][C:22]=2[N:23]=1)[C:10]#[N:11].C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>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:25])=[N:23][C:22]=2[CH:21]=[CH:20][N:19]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 76113BromotrimethylsilaneHCID 866689933,5-Dichloro-4-(4-chloro-thiazolo[5,4-c]pyridine-2-yl)-benzonitrile

Product 1

HCID 866689964-(4-Bromothiazolo[5,4-c]pyridin-2-yl)-3,5-dichlorobenzonitrileYield 96.1%

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Conditions

Temperature
90 °C

Procedure

Trimethylsilylbromide (0.23 mL, 1.74 mmol) was added to a stirred solution of 3,5-dichloro-4-(4-chloro-thiazolo[5,4-c]pyridine-2-yl)-benzonitrile (295 mg, 0.87 mmol) in propionitrile (11 mL) and the mixture heated at 90° C. for 48 hours. The reaction mixture was allowed to cool and poured onto a mixture of saturated aqueous potassium carbonate solution and ice. DCM was added and the organic phase was separated, dried over Na2SO4 and concentrated to dryness under reduced pressure to give the desired compound as a white solid (322 mg, 96% yield). 1H NMR (300 MHz, CDCl3): δ 8.53 (d, J=5.5 Hz, 1H), 8.03-8.00 (m, 1H), 7.80 (s, 2H). LCMS (Method D): RT=4.04 min, m/z: 386 [M+H+].

Workup

  1. temperatureto cool
  2. customthe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-56632a201090498f8f73e3a8350fb486
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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