Dimethylformamide → HCID 56940970, compound

HRID 1844074Notes

Reaction equation

HRID 1844074 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[Cl:17])[C:13](=[O:18])[N:12]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:24]=1[CH:25]1[CH2:27][CH2:26]1)[CH2:11][CH2:10]2)(=O)=O.[CH3:30][N:31](C=O)C>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].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.[C-]#N.[Zn+2]>[Cl:17][C:16]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][N:12]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][C:24]=3[CH:25]3[CH2:27][CH2:26]3)[C:13]2=[O:18])=[CH:8][C:7]=1[C:30]#[N:31]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 87158322HCID 87158322, compound

Product 1

HCID 56940970HCID 56940970, compoundYield 24.3%

Reagents, catalysts & solvents 3

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

Procedure

7-Chloro-2-(4-cyclopropylpyridin-3-yl)-1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl trifluoromethanesulfonate (I-91a: 170 mg, 0.381 mmol) in DMF (3 mL) was reacted with Pd2(dba)3 (6.97 mg, 0.007 mmol), dppf (16.9 mg, 0.003 mmol) and Zn(CN)2 (26.8 mg, 0.228 mmol) for 24 hours at 80° C. to afford the crude product. Purification by column chromatography on silica gel (2% methanol in CHCl3) followed by preparative HPLC afforded 30 mg of the product (24.3% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (2% methanol in CHCl3)

Sources & evidence

ORD record
ord-e8b912dad741495abf1006cd325390c0
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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