Borane;tetrahydrofuran → HCID 70979847, compound

HRID 1485381Notes

Reaction equation

HRID 1485381 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:14](=O)[C:13]([CH3:17])([CH3:16])[C:12]3=[N:18][N:19]=[C:20]([CH3:21])[N:11]3[C:10]3[CH:22]=[CH:23][CH:24]=[CH:25][C:9]2=3)=[CH:4][CH:3]=1.B.C1COCC1>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:14][C:13]([CH3:17])([CH3:16])[C:12]3=[N:18][N:19]=[C:20]([CH3:21])[N:11]3[C:10]3[CH:22]=[CH:23][CH:24]=[CH:25][C:9]2=3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 70978986HCID 70978986, compound

Product 1

HCID 70979847HCID 70979847, compoundYield 10.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a THF (5 ml) solution of 6-(4-chlorophenyl)-1,4,4-trimethyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one of (51 mg, 0.14 mmol) was added BH3-THF complex (1 mL, 1M in THF) drop-wise at 0° C. The resulting mixture was heated at reflux overnight, then the mixture was concentrated in vacuo and the residue was purified by Prep-TLC (silica-gel, DCM:methanol=10:1) to give 6-(4-chlorophenyl)-1,4,4-trimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine as a white solid (5.0 mg, yield 10.4%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux overnight
  3. concentrationthe mixture was concentrated in vacuo
  4. customthe residue was purified by Prep-TLC (silica-gel, DCM:methanol=10:1)

Sources & evidence

ORD record
ord-170a07f3fbbd422c9b5d3798869c4ddf
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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