Dimethylformamide → HCID 178418825, compound

HRID 10566

Reaction equation

HRID 10566 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([O:15][C:16]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:17]=2[C:18](Br)=[CH:19][N:20]=[CH:21]3)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:27][N:28](C=O)C>[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].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([O:15][C:16]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:17]=2[C:18]([C:27]#[N:28])=[CH:19][N:20]=[CH:21]3)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 178418932HCID 178418932, compound

Product 1

HCID 178418825HCID 178418825, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
120 °C

Procedure

A suspension of Intermediate 121 (113.7 mg), zinc cyanide (19.4 mg, Wako Pure Chemical Industries), tris(dibenzylideneacetone)dipalladium(0) (24.0 mg) and 1,1′-bis(diphenylphosphino)ferrocene (35.3 mg, Tokyo Kasei Kogyo) in DMF (2 ml) was stirred at 120° C. for 19 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain the title compound (34.9 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-77836b6fe0cb4c828f1476a14df81196
Source dataset
uspto-grants-2006_08
Patent number
US07094789B2

Linked notes

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