5-Chloro-2-fluorobenzoyl chloride → (2Z)-2-(3-butyl-4-methyl-1,3-thiazol-2(3H)-ylidene)-1-(5-chloro-2-fluorophenyl)ethanone

HRID 448035Notes

Reaction equation

HRID 448035 reaction equation
[I-].[CH2:2]([N+:6]1[C:10]([CH3:11])=[CH:9][S:8][C:7]=1[CH3:12])[CH2:3][CH2:4][CH3:5].[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([F:23])=[C:18]([CH:22]=1)[C:19](Cl)=[O:20]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CS(C)=O.CO>[CH2:2]([N:6]1[C:10]([CH3:11])=[CH:9][S:8]/[C:7]/1=[CH:12]\[C:19]([C:18]1[CH:22]=[C:14]([Cl:13])[CH:15]=[CH:16][C:17]=1[F:23])=[O:20])[CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 2

HCID 27736045-Chloro-2-fluorobenzoyl chlorideHCID 691651093-Butyl-2,4-dimethylthiazol-3-ium iodide

Product 1

HCID 69321127(2Z)-2-(3-butyl-4-methyl-1,3-thiazol-2(3H)-ylidene)-1-(5-chloro-2-fluorophenyl)ethanone

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×HCID 22036561Dimethyl sulfoxide methanolSolvent

Procedure

In a 20 mL vial a solution of 3-butyl-2,4-dimethylthiazol-3-ium iodide (47.92 mg, 0.16 mmol) dissolved in CH2Cl2 (0.5 mL) was added, followed by the addition of DMAP (49.24 mg, 0.40 mmol) dissolved in CH2Cl2 (0.8 mL). Then, to the solution was added 5-chloro-2-fluorobenzoyl chloride (30.9 mg, 0.16 mmol) dissolved in CH2Cl2 (0.5 mL). The vial was capped and shaken overnight at room temperature. The residue was dissolved in 1:1 DMSO/MeOH and purified by reverse phase HPLC using a method analogous to that described in Example 53 to provide the title compound. 1H NMR (500 MHz, DMSO-d6/D2O) δ ppm 0.95 (t, 3 H) 1.31-1.41 (m, 2 H) 1.57-1.77 (m, 2 H) 2.28-2.34 (m, 3 H) 3.95-4.02 (m, 2 H) 6.37-6.41 (m, 1 H) 6.55-6.68 (m, 1 H) 7.28-7.35 (m, 1 H) 7.48-7.54 (m, 1 H) 7.76-7.80 (m, 1 H); MS (ESI) positive ion 326 (M+H).

Workup

  1. additionwas added
  2. customThe vial was capped
  3. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-44b24e79dbd443248ff86fd9a24d2e62
Source dataset
uspto-grants-2013_07
Patent number
US08481574B2

Reaction notes

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