Nitrogen → HCID 18466623, compound
Reaction equation
[CH2:1]([Sn](CCCC)(CCCC)CCCC)[CH:2]=[CH2:3].N#N.Br[C:20]1[CH:39]=[N:38][C:23]2[N:24]([CH2:36][CH3:37])[C:25]3[N:33]=[C:32]([F:34])[CH:31]=[C:30]([CH3:35])[C:26]=3[NH:27][C:28](=[O:29])[C:22]=2[CH:21]=1.O>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>[CH2:36]([N:24]1[C:23]2[N:38]=[CH:39][C:20]([CH2:3][CH:2]=[CH2:1])=[CH:21][C:22]=2[C:28](=[O:29])[NH:27][C:26]2[C:30]([CH3:35])=[CH:31][C:32]([F:34])=[N:33][C:25]1=2)[CH3:37]Participants
7
Conditions
- Temperature
- 90 °C
Procedure
Allyltributyltin (7.77 mL, 25.1 mmol) and Pd(Ph3P)4 (1.32 g, 1.14 mmol) were added to a degassed (N2 through solution for 30 min) solution of 8-bromo-5,11-dihydro-11-ethyl-2-fluoro-4-methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (8.0 g, 22.8 mmol) in DMF (114 mL). The mixture was heated to 90° C. for 3 h. The mixture was poured into water (250 mL) and extracted with EtOAc (4×250 mL). The combined organic layers were washed with 20% aqueous NH40H (250 mL) and brine (250 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (hexanes:EtOAc, 4:1 to 1:1) to give the title compound (3.16 g, 51% yield).
Workup
- extractionextracted with EtOAc (4×250 mL)
- washThe combined organic layers were washed with 20% aqueous NH40H (250 mL) and brine (250 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by flash chromatography (hexanes:EtOAc, 4:1 to 1:1)
Sources & evidence
- ORD record
- ord-7dd0526967164bf5a33d5b9d78b93ee8
- Source dataset
- uspto-grants-2002_07
- Patent number
- US06420359B1
Reaction notes
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