Hydrochloric Acid → HCID 86614856, compound

HRID 2080629Notes

Reaction equation

HRID 2080629 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]([C:5]1[NH:9][C:8]2[CH:10]=[C:11]([C:16]([F:19])([F:18])[F:17])[C:12]([C:14]#[N:15])=[CH:13][C:7]=2[N:6]=1)=[O:4].Br[CH2:23][C:24]#[C:25][CH3:26].[In].Cl>C1COCC1.O.C(OCC)(=O)C>[OH:4][C:3]([C:5]1[NH:9][C:8]2[CH:10]=[C:11]([C:16]([F:17])([F:18])[F:19])[C:12]([C:14]#[N:15])=[CH:13][C:7]=2[N:6]=1)([C:2]([F:20])([F:1])[F:21])[C:25]([CH3:26])=[C:24]=[CH2:23]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 27568621-Bromo-2-butyneHCID 5359967IndiumHCID 86614855HCID 86614855, compound

Product 1

HCID 86614856HCID 86614856, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(2,2,2-Trifluoro-acetyl)-6-trifluoromethyl-1H-benzoimidazole-5-carbonitrile (0.31 g; 0.94 mmol), 1-bromo-2-butyne (0.85 mL; 9.4 mmol) and indium (1.09 g; 9.5 mmol) were suspended in THF (12 mL) and 0.03 M HCl (10 mL) and stirred vigorously overnight. The reaction mixture was then 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 to yield a crude material. The crude material was purified by column chromatography (SiO2; 20% ethyl acetate/hexanes) to yield the title compound as a 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. customto yield a crude material
  6. customThe crude material was purified by column chromatography (SiO2; 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-9b7ddd02ecde4fd7aa71e49ab56aa73d
Source dataset
uspto-grants-2011_04
Patent number
US07932399B2

Reaction notes

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