Boron trifluoride etherate → HCID 178427341, compound

HRID 2173993Notes

Reaction equation

HRID 2173993 reaction equation
[CH3:1][C:2]1[C:3]([CH:22]([OH:42])[C:23]2[N:27](COCC[Si](C)(C)C)[C:26]3[CH:36]=[CH:37][C:38]([C:40]#[N:41])=[CH:39][C:25]=3[N:24]=2)=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7]([S:12]([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.CC1C(C(O)C2N(COCC[Si](C)(C)C)C3C=C(C#N)C=CC=3N=2)=C2C(=C(C)C=1)N(S(C1C=CC(C)=CC=1)(=O)=O)C=C2.B(F)(F)F.CCOCC>C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>[CH3:1][C:2]1[C:3]([CH:22]([OH:42])[C:23]2[NH:27][C:26]3[CH:36]=[CH:37][C:38]([C:40]#[N:41])=[CH:39][C:25]=3[N:24]=2)=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7]([S:12]([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:6]=[CH:5]2

Participants

7

Reactant 3

HCID 8000Boron trifluoride etherateHCID 86701562HCID 86701562, compoundHCID 86701563HCID 86701563, compound

Product 1

HCID 178427341HCID 178427341, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Procedure

To a solution of (±)-2-((5,7-dimethyl-1-tosyl-1H-indol-4-yl)(hydroxy)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-5-carbonitrile and (±)-2-((5,7-dimethyl-1-tosyl-1H-indol-4-yl)(hydroxy)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-6-carbonitrile (90 mg, 0.150 mmol) in CH2Cl2 (1.5 mL), BF3.OEt2 (0.095 mL, 0.749 mmol) was added at 0° C. After stirring for 5 min., the mixture was warmed to room temperature. After stirring for 1 h, the reaction mixture was diluted with 2M aq. Na2CO3 and EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to give the title compound, without need of further purification. MS (ESI+) m/z 471 (M+H).

Workup

  1. stirringAfter stirring for 1 h
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-40816afb2bdf413db822ae8ca6b4960d
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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