Lithium tetrafluoroborate → HCID 178427311, compound

HRID 2174023Notes

Reaction equation

HRID 2174023 reaction equation
[OH:1][C:2]1([C:26]2[N:30](COCC[Si](C)(C)C)[C:29]3[CH:39]=[C:40]([C:43]#[N:44])[CH:41]=[CH:42][C:28]=3[N:27]=2)[C:12]2[C:13]3[C:5](=[CH:6][N:7]([S:16]([C:19]4[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=4)(=[O:18])=[O:17])[C:8]=3[C:9]([CH3:15])=[CH:10][C:11]=2[CH3:14])[CH2:4][CH2:3]1.OC1(C2N(COCC[Si](C)(C)C)C3C=CC(C#N)=CC=3N=2)C2C3C(=CN(S(C4C=CC(C)=CC=4)(=O)=O)C=3C(C)=CC=2C)CC1.F[B-](F)(F)F.[Li+]>O>[OH:1][C:2]1([C:26]2[NH:27][C:28]3[CH:42]=[CH:41][C:40]([C:43]#[N:44])=[CH:39][C:29]=3[N:30]=2)[C:12]2[C:13]3[C:5](=[CH:6][N:7]([S:16]([C:19]4[CH:20]=[CH:21][C:22]([CH3:23])=[CH:24][CH:25]=4)(=[O:18])=[O:17])[C:8]=3[C:9]([CH3:15])=[CH:10][C:11]=2[CH3:14])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 4298216Lithium tetrafluoroborateHCID 86701623HCID 86701623, compoundHCID 86701624HCID 86701624, compound

Product 1

HCID 178427311HCID 178427311, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of (±)-2-(5-hydroxy-6,8-dimethyl-1-tosyl-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-6-carbonitrile and (±)-2-(5-hydroxy-6,8-dimethyl-1-tosyl-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-5-carbonitrile (50 mg, 0.08 mmol), lithium tetrafluoroborate (1.5 mL, 1.5 mmol) and H2O (0.15 mL) were added. The reaction was heated to 70° C. overnight. It was quenched with a sat. NaHCO3 solution. The layers were separated and the aqueous layer was extracted with EtOAc. It was purified using FCC eluting with heptane:EtOAc 1:2 to give the title compound. MS (ESI+) m/z 497.4 (M+H).

Workup

  1. additionwere added
  2. customIt was quenched with a sat. NaHCO3 solution
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc
  5. customIt was purified
  6. washeluting with heptane:EtOAc 1:2

Sources & evidence

ORD record
ord-e7655cb6a5334df59c7b29c4e2b61a94
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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