Triethylamine → HCID 86585107, compound

HRID 430670Notes

Reaction equation

HRID 430670 reaction equation
I[C:2]1[N:3]=[C:4]2[CH2:10][C:9]3[CH:11]=[C:12]4[O:17][CH2:16][O:15][C:13]4=[CH:14][C:8]=3[C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:6][N:5]2[C:24]=1[CH3:25].C(N(CC)CC)C.[P:33]([O-:40])([O:37][CH2:38][CH3:39])[O:34][CH2:35][CH3:36]>CN(C)C=O.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH2:35]([O:34][P:33]([C:2]1[N:3]=[C:4]2[CH2:10][C:9]3[CH:11]=[C:12]4[O:17][CH2:16][O:15][C:13]4=[CH:14][C:8]=3[C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:6][N:5]2[C:24]=1[CH3:25])(=[O:40])[O:37][CH2:38][CH3:39])[CH3:36]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 3780918DiethylphosphiteHCID 18183184HCID 18183184, compound

Product 1

HCID 86585107HCID 86585107, compoundYield 10.1%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

100 mg of 9-iodo-8-methyl-5-phenyl-11H-1,3-dioxolo[4,5-h]imidazo[1,2-c][2,3]benzodiazepine is stirred in 2 ml of dimethylformamide, 0.03 ml of triethylamine, 0.032 ml (30 mg) of diethyl phosphite and 15 mg of tetrakis(triphenylphosphine)-palladium(O) at 100° C. for 2 hours. Then, it is diluted with 10 ml of water and extracted with ethyl acetate. The organic phase that is concentrated by evaporation is chromatographed on silica gel with dichloromethane:ethanol=95:5 as an eluant. 10 mg of 8-methyl-5-phenyl-11H-1,3-dioxolo[4,5-h]imidazo[1,2-c][2,3]benzodiazepine-9-phosphonic acid diethyl ester is obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic phase that is concentrated by evaporation
  3. customis chromatographed on silica gel with dichloromethane

Sources & evidence

ORD record
ord-9b7c66a979e8455091ea08c4a8948313
Source dataset
uspto-grants-2001_11
Patent number
US06323197B1

Reaction notes

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