Triethylamine → 5,11-Dihydro-11-ethyl-5-methyl-8-phenylethynyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 724940Notes

Reaction equation

HRID 724940 reaction equation
[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12](I)=[CH:13][C:8]=2[C:7](=[O:15])[N:6]([CH3:16])[C:5]2[CH:17]=[CH:18][CH:19]=[N:20][C:4]1=2)[CH3:2].[C:21]1([C:27]#[CH:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12]([C:28]#[C:27][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:13][C:8]=2[C:7](=[O:15])[N:6]([CH3:16])[C:5]2[CH:17]=[CH:18][CH:19]=[N:20][C:4]1=2)[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 10547779HCID 10547779, compound

Product 1

HCID 105701215,11-Dihydro-11-ethyl-5-methyl-8-phenylethynyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-oneYield 53.2%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 5,11-dihydro-11-ethyl-8-iodo-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.20 g, 0.53 mmol), phenylacetylene (0.06 mL, 0.55 mmol), bis(triphenylphosphine)palladium(II) chloride (25 mg, 0.04 mmol), and triethylamine (0.16 mL, 1.14 mmol) in 3 mL of N,N-dimethylformamide was heated at 95° C. under argon for 19 hours. Workup as described in Example 1h and purification by flash chromatography, eluting with ethyl acetate/dichloromethane, afforded 0.1 g of the title compound.

Workup

  1. customWorkup as described in Example 1h and purification by flash chromatography
  2. washeluting with ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-d442a604ec0f47059bf4d734a4246034
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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