Water → 5-Chloro-7,8-dimethoxy-1-n-propyl-1,3-dihydro-1,4-benzodiazepin-2-one

HRID 1297097Notes

Reaction equation

HRID 1297097 reaction equation
[Cl:1][C:2]1[C:8]2[CH:9]=[C:10]([O:15][CH3:16])[C:11]([O:13][CH3:14])=[CH:12][C:7]=2[N:6]([CH3:17])[C:5](=[O:18])[CH2:4][N:3]=1.[C:19]1(B(O)O)C=CC=C[CH:20]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>CN(C=O)C>[Cl:1][C:2]1[C:8]2[CH:9]=[C:10]([O:15][CH3:16])[C:11]([O:13][CH3:14])=[CH:12][C:7]=2[N:6]([CH2:17][CH2:19][CH3:20])[C:5](=[O:18])[CH2:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 691548525-Chloro-7,8-dimethoxy-1-methyl-1,3-dihydro-1,4-benzodiazepin-2-one

Product 1

HCID 694609705-Chloro-7,8-dimethoxy-1-n-propyl-1,3-dihydro-1,4-benzodiazepin-2-oneYield 55.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

Heat at 115° C. for 12 hours under an inert atmosphere a mixture of 200 mg (0.74 mmol) of 5-chloro-7,8-dimethoxy-1-methyl-1,3-dihydro-1,4-benzodiazepin-2-one XVIIIaa, 109 mg (0.89 mmol) of benzene boronic acid, 182 mg (0.86 mmol) of K3PO4, 23 mg (0.020 mmol) of tetrakis(triphenylphosphine)Pd(0) in 5 ml of DMF. Allow to cool to room temperature. Add 80 ml of H2O and extract three times with 50 ml of Et2O. Dry the organic fractions on Na2SO4. Purify by chromatography (AcOEt). Recrystallize in EtOH. One obtains 122 mg of the abovenamed product in the form of colorless crystals.

Workup

  1. temperatureto cool to room temperature
  2. extractionextract three times with 50 ml of Et2O
  3. customDry the organic fractions on Na2SO4
  4. customPurify by chromatography (AcOEt)
  5. customRecrystallize in EtOH

Sources & evidence

ORD record
ord-f5a3bffe676b4aca9ec5a97b8b29b404
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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