Nitrogen → HCID 57554620, compound

HRID 1511882Notes

Reaction equation

HRID 1511882 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:19][CH2:18][C:10]3([NH:14][C:13](=[O:15])[N:12]([CH3:16])[C:11]3=[O:17])[CH2:9]2)=[CH:4][CH:3]=1.N#N.[CH3:22][N:23]1C(=O)CCC1>[Zn].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:16][N:12]1[C:11](=[O:17])[C:10]2([CH2:18][CH2:19][C@H:8]([C:5]3[CH:6]=[CH:7][C:2]([C:22]#[N:23])=[CH:3][CH:4]=3)[CH2:9]2)[NH:14][C:13]1=[O:15]

Participants

8

Reactant 3

HCID 947NitrogenHCID 13387N-methyl-2-pyrrolidoneHCID 44191844HCID 44191844, compound

Product 1

HCID 57554620HCID 57554620, compound

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
120 °C

Procedure

A suspension of (7S)-7-(4-bromophenyl)-3-methyl-1,3-diazaspiro[4.4]nonane-2,4-dione (General procedures A, B, C) (0.500 g, 1.547 mmol) in anhydrous NMP (4.00 ml) was degassed by evacuating the reaction vial then refilling with N2 a couple of times. To this suspension was added zinc (1.012 mg, 0.015 mmol), dppf (0.027 g, 0.048 mmol), zinc cyanide (0.145 g, 1.238 mmol), and Pd2(dba)3 (0.021 g, 0.023 mmol) at ambient temperature. The resulting mixture was heated to 120° C. for about 16 hours. The crude material was filtered through Celite®. The filtrate was taken up in water (70 mL) and ethyl acetate (100 mL). The organic phase was washed with water (50 mL×2) and brine (50 mL), dried (MgSO4) and concentrated to yield 4-((7S)-3-methyl-2,4-dioxo-1,3-diazaspiro[4.4]nonan-7-yl)benzonitrile (0.44 g, 0.20 mmol) as light brown solid.

Workup

  1. customwas degassed
  2. customby evacuating
  3. customthe reaction vial
  4. filtrationThe crude material was filtered through Celite®
  5. washThe organic phase was washed with water (50 mL×2) and brine (50 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9e6a2b87131946eabaf34baf56eb34da
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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