1-Bromopent-2-yne → HCID 58333165, compound

HRID 2037226Notes

Reaction equation

HRID 2037226 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][CH2:22][CH3:23].[In]>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]([CH2:22][CH3:23])=[C:20]=[CH2:19])[C:10]([F:13])([F:11])[F:12])=[N:6][C:5]=2[CH:15]=1

Participants

7

Reactant 3

HCID 853991-Bromopent-2-yneHCID 5359967IndiumHCID 115943701-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone

Product 1

HCID 58333165HCID 58333165, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(5,6-Dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone (2 g), 1-bromo-2-pentyne (1.1 ml) and indium (983 mg) were suspended in THF (15 mL) and H2O (45 mL) and stirred vigorously overnight. The reaction mixture was then diluted with water and ethyl acetate, the layers were separated and the aqueous layer was extracted with ethyl acetate. The combined extracts were washed with brine and dried over Na2SO4 to yield a crude material. The crude material was purified by column chromatography (SiO2; 5-30% ethyl acetate/hexanes) to yield the title compound as a peach-colored solid.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. customto yield a crude material
  6. customThe crude material was purified by column chromatography (SiO2; 5-30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-96984360b4ac4118b6f0960bd3f375f9
Source dataset
uspto-grants-2013_11
Patent number
US08575206B2

Reaction notes

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