Trichloroacetyl chloride → HCID 58379327, compound

HRID 408797Notes

Reaction equation

HRID 408797 reaction equation
[C:1]([C:4]1[N:5]=[C:6]2[C:11]([C:12]([NH2:14])=O)=[CH:10][CH:9]=[CH:8][N:7]2[C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.ClC(Cl)(Cl)C(Cl)=O>ClCCl>[C:1]([C:4]1[N:5]=[C:6]2[C:11]([C:12]#[N:14])=[CH:10][CH:9]=[CH:8][N:7]2[C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 58379321HCID 58379321, compound

Product 1

HCID 58379327HCID 58379327, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

A solution of 2-acetyl-3-(3-fluorophenyl)imidazo[1,2-a]pyridine-8-carboxamide (0.24 g, 0.81 mmol) in dichloromethane (12 mL) was treated with triethylamine (0.34 mL, 2.4 mmol) and cooled to −15° C. The reaction mixture was treated with trichloroacetyl chloride (0.18 mL, 1.6 mmol) dropwise and stirred between −15° C. to −10° C. for 1 h. The reaction mixture was diluted with dichloromethane (100 mL) and washed with water (2×50 mL) and brine (50 mL), dried with sodium sulfate, filtered, and concentrated to give the desired product (0.23 g, quantitative). This material was used without further purification. LCMS for C16H11FN3O (M+H)+: m/z=280.1.

Workup

  1. washwashed with water (2×50 mL) and brine (50 mL)
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6150bc30a1404098a4b6e91d0330ff91
Source dataset
uspto-grants-2014_06
Patent number
US08759359B2

Reaction notes

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