Nitrogen → HCID 18466626, compound

HRID 2229350Notes

Reaction equation

HRID 2229350 reaction equation
[CH2:1]([Sn](CCCC)(CCCC)CCCC)[CH:2]=[CH2:3].N#N.Br[C:20]1[CH:42]=[N:41][C:23]2[N:24]([CH2:39][CH3:40])[C:25]3[N:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[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>[CH2:39]([N:24]1[C:23]2[N:41]=[CH:42][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]([C:35]([F:38])([F:37])[F:36])=[N:34][C:25]1=2)[CH3:40]

Participants

6

Reactant 3

HCID 947NitrogenHCID 90628AllyltributylstannaneHCID 18466620HCID 18466620, compound

Product 1

HCID 18466626HCID 18466626, compoundYield 103.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Allyltributyltin (98 μL, 0.32 mmol) and Pd(Ph3P)4 (16 mg, 0.02 mmol) were added to a degassed (N2 through solution for 30 min) solution of 8-bromo-5,11-dihydro-11-ethyl-5-methyl-2-(trifluoromethyl)-6H-dipyrido[3,2-b:2′,3′-e] [1,4]diazepin-6-one (11 mg, 0.27 mmol) in DMF (1.4 mL) at room temperature. The mixture was stirred at 90° C. for 1.5 h then was cooled to room temperature and concentrated under reduced pressure. The residue was purified by flash chromatography (hexane:EtOAc, 8:2 to 7:3) to give the title compound (101 mg, 99% yield).

Workup

  1. temperaturethen was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by flash chromatography (hexane:EtOAc, 8:2 to 7:3)

Sources & evidence

ORD record
ord-2ca0ad9cda2d442eaad802c72da6e634
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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