2,6-Di-tert-butyl-4-methylphenol → 13-Benzyl-2-ethyl-9-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-one

HRID 724962Notes

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]([C:25]1[CH:30]=[C:29](C)[CH:28]=[C:27](C(C)(C)C)[C:26]=1O)(C)(C)C.C([Sn](CCCC)(CCCC)CCCC)C1C=CC=CC=1.[F-].[K+]>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>[CH2:21]([C:12]1[CH:11]=[N:10][C:9]2[N:3]([CH2:1][CH3:2])[C:4]3[N:20]=[CH:19][CH:18]=[CH:17][C:5]=3[N:6]([CH3:16])[C:7](=[O:15])[C:8]=2[CH:13]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 5,11-dihydro-11-ethyl-8-iodo-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.3 g, 0.79 mmol), bis(triphenylphosphine)palladium(II) chloride (18 mg, 0.03 mmol), and 2,6-di-tert-butyl-4-methylphenol (1 crystal) in 5 mL of N,N-dimethylformamide was added benzyltributylstannane (0.36 g, 0.94 mmol). The resultant reaction mixture was heated at 100° C. under argon for 5 hours. An aqueous solution of potassium fluoride was added and the mixture was stirred for 5 hours. The product was extracted with dichloromethane and purified by flash chromatography, eluting with ethyl acetate/dichloromethane, to give 20 mg of the title compound as an oil.

Workup

customThe resultant reaction mixture
extractionThe product was extracted with dichloromethane
custompurified by flash chromatography
washeluting with ethyl acetate/dichloromethane

Sources & evidence

ORD record: ord-9179948f6de94dbb8baf60c010db5789
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05705499

Reaction notes

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