Boron trifluoride etherate → HCID 178427331, compound

HRID 2173989Notes

Reaction equation

HRID 2173989 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:33][O:34]COCC[Si](C)(C)C)[C:5]([CH2:21][C:22]2[NH:26][C:25]3[CH:27]=[CH:28][C:29]([C:31]#[N:32])=[CH:30][C:24]=3[N:23]=2)=[C:6]2[C:10]=1[N:9]([S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:8]=[CH:7]2.B(F)(F)F.O(CC)CC>C(Cl)Cl>[OH:34][CH2:33][C:4]1[C:5]([CH2:21][C:22]2[NH:26][C:25]3[CH:27]=[CH:28][C:29]([C:31]#[N:32])=[CH:30][C:24]=3[N:23]=2)=[C:6]2[C:10](=[C:2]([CH3:1])[CH:3]=1)[N:9]([S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 178427332HCID 178427332, compound

Product 1

HCID 178427331HCID 178427331, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-((7-methyl-1-tosyl-5-(((2-(trimethylsilyl)ethoxy)methoxy)methyl)-1H-indol-4-yl)methyl)-1H-benzo[d]imidazole-5-carbonitrile (133 mg, 0.221 mmol) in CH2Cl2 (10 mL) was added BF3-OEt2 (0.084 mL, 0.664 mmol) at 0° C. The whole mixture was stirred at 0° C. for 1.5 h, and then at room temperature for 2.5 h. The reaction was quenched by 5% aq. NaHCO3 and stirred for 0.5 h. The layers were separated and the aqueous layer was extracted with CH2Cl2. The organic layers were combined and washed with H2O and brine, dried over Na2SO4, and filtered. Concentration of the filtrate gave the title compound, without need of further purification. MS (ESI+) m/z 471.1 (M+H).

Workup

  1. waitat room temperature for 2.5 h
  2. customThe reaction was quenched by 5% aq. NaHCO3
  3. stirringstirred for 0.5 h
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with CH2Cl2
  6. washwashed with H2O and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered

Sources & evidence

ORD record
ord-4dbcf0c4559b4e7c9481ce10f166e0ee
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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