Hydrochloric Acid → HCID 23729187, compound

HRID 2037203Notes

Reaction equation

HRID 2037203 reaction equation
[Cl:1][C:2]1[C:16]([Cl:17])=[CH:15][C:5]2[NH:6][C:7]([C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])=[N:8][C:4]=2[CH:3]=1.Br[CH2:19][C:20]#[C:21][CH3:22].[In].Cl>C1COCC1.O.C(OCC)(=O)C>[Cl:17][C:16]1[C:2]([Cl:1])=[CH:3][C:4]2[NH:8][C:7]([C:9]([OH:14])([C:21]([CH3:22])=[C:20]=[CH2:19])[C:10]([F:13])([F:11])[F:12])=[N:6][C:5]=2[CH:15]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 27568621-Bromo-2-butyneHCID 5359967IndiumHCID 115943701-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone

Product 1

HCID 23729187HCID 23729187, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(5,6-Dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone (0.61 g; 2.2 mmol), 1-bromo-2-butyne (1.7 mL; 18.8 mmol) and indium (2.49 g; 21.7 mmol) were suspended in THF (10 mL) and 0.045 M HCl (20 mL) and stirred vigorously overnight. The reaction mixture was diluted with water (60 mL) and ethyl acetate (40 mL), the layers were separated and the aqueous layer was extracted with ethyl acetate (3×20 mL). The combined extracts were washed with brine (50 mL) and dried over Na2SO4. The resulting crude material was purified by column chromatography (SiO2; 20% ethyl acetate/hexanes) to yield the title compound as an off-white solid.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×20 mL)
  3. washThe combined extracts were washed with brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. customThe resulting crude material was purified by column chromatography (SiO2; 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-180c6e0f92684caa82b33ba87b1cb254
Source dataset
uspto-grants-2013_11
Patent number
US08575206B2

Reaction notes

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