Nitrogen → HCID 18753043, compound

HRID 2229318Notes

Reaction equation

HRID 2229318 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:34]=[C:33]([F:35])[CH:32]=[CH:31][C:26]=3[N:27]([CH3:30])[C:28](=[O:29])[C:22]=2[CH:21]=1>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])[N:27]([CH3:30])[C:26]2[CH:31]=[CH:32][C:33]([F:35])=[N:34][C:25]1=2)[CH3:37]

Participants

6

Reactant 3

HCID 947NitrogenHCID 90628AllyltributylstannaneHCID 108078258-Bromo-2-fluoro-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Product 1

HCID 18753043HCID 18753043, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Allyltributyltin (32.0 mL, 103.4 mmol) and Pd(Ph3P)4 (5.43 g, 4.70 mmol) were added to a degassed (N2 through solution for 45 min) solution of 8-bromo-5,11-dihydro-11-ethyl-2-fluoro-5-methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (33.0 g, 94.0 mmol) in DMF (470 mL). Additional amounts of Pd(Ph3)4 (1.09 g, 0.94 mmol added after 1, 2,3,4,5 h of reaction) were added to complete the reaction. The mixture was heated to 90° C. for 6 h. The mixture was concentrated under reduced pressure. The residue was purified by flash chromatography (hexanes:EtOAc, 8:2 to 7:3) to give the title compound (22.4 g, 76% yield).

Workup

  1. customthe reaction
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography (hexanes:EtOAc, 8:2 to 7:3)

Sources & evidence

ORD record
ord-504ff056c8414ccb9c123993797ef516
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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