Allyltributylstannane → 2-Chloro-5,11-dihydro-11-ethyl-4-methyl-8-(2-propenyl)-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 2229323Notes

Reaction equation

Br[C:2]1[CH:21]=[N:20][C:5]2[N:6]([CH2:18][CH3:19])[C:7]3[N:15]=[C:14]([Cl:16])[CH:13]=[C:12]([CH3:17])[C:8]=3[NH:9][C:10](=[O:11])[C:4]=2[CH:3]=1.[CH2:22]([Sn](CCCC)(CCCC)CCCC)[CH:23]=[CH2:24]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:16][C:14]1[CH:13]=[C:12]([CH3:17])[C:8]2[NH:9][C:10](=[O:11])[C:4]3[CH:3]=[C:2]([CH2:24][CH:23]=[CH2:22])[CH:21]=[N:20][C:5]=3[N:6]([CH2:18][CH3:19])[C:7]=2[N:15]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 8-bromo-2-chloro-5,11-dihydro-11-ethyl-4-methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (12.6 g, 34.3 mmol) in DMF (25-0 mL) was degassed under reduced pressure for 20 min. Pd(PPh3)4 (775 mg, 0.7 mmol) was then added followed by allyltributyltin (12.5 mL, 41.1 mmol). After degassing under reduced pressure for 10 min, the mixture was heated to 100° C. for 7 h. The mixture was then concentrated under reduced pressure. The residue was purified by flash chromatography (hexane:EtOAc, 19:1) to give the title compound (8.04 g, 71% yield) as a yellow solid.

Workup

customAfter degassing under reduced pressure for 10 min
concentrationThe mixture was then concentrated under reduced pressure
customThe residue was purified by flash chromatography (hexane:EtOAc, 19:1)

Sources & evidence

ORD record: ord-ea34600dd94e4ccbbb35ca199c51fa6e
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06420359B1

Reaction notes

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