Boron trifluoride etherate → HCID 178427329, compound

HRID 2174059Notes

Reaction equation

HRID 2174059 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH3:42])[C:6]([CH2:22][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:7]2[C:11]=1[N:10]([S:12]([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:9]=[CH:8]2.OCC1C=C(C)C(CC2N(COCC[Si](C)(C)C)C3C=C(C#N)C=CC=3N=2)=C2C=1N(S(C1C=CC(C)=CC=1)(=O)=O)C=C2.B(F)(F)F.CCOCC>C(Cl)Cl.C([O-])(O)=O.[Na+].CCOC(C)=O>[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH3:42])[C:6]([CH2:22][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:7]2[C:11]=1[N:10]([S:12]([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:9]=[CH:8]2

Participants

7

Reactant 3

HCID 8000Boron trifluoride etherateHCID 86701683HCID 86701683, compoundHCID 86701684HCID 86701684, compound

Product 1

HCID 178427329HCID 178427329, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of a mixture of 2-((7-(hydroxymethyl)-5-methyl-1-tosyl-1H-indol-4-yl)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-5-carbonitrile and 2-((7-(hydroxymethyl)-5-methyl-1-tosyl-1H-indol-4-yl)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-6-carbonitrile (14 mg, 0.023 mmol) in DCM (0.23 mL), BF3.OEt2 (15 μL, 0.117 mmol) was added at 0° C. After stirring for 5 minutes, the mixture was warmed up to room temperature. After 30 minutes the reaction mixture was diluted with sat. aq. NaHCO3 and EtOAc, extracted with EtOAc, and the organic extract was dried over MgSO4, filtered and concentrated to provide the title compound, which was used without further purification. MS (ESI+) m/z 471.2 (M+H).

Workup

  1. additionwas added at 0° C
  2. extractionextracted with EtOAc
  3. extractionthe organic extract
  4. dry with materialwas dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-534c8b7a4fe447a5b73d212d079336d1
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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