Dimethylacetamide → HCID 68427635, compound

HRID 642463Notes

Reaction equation

HRID 642463 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:26])=[C:8]2[C:15]([Cl:16])=[C:14]([Cl:17])[N:13]([CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:9]2=[C:10](Cl)[N:11]=1)=[O:5])[CH3:2].C[C:28]([N:30](C)C)=O>[C-]#N.[C-]#N.[Zn+2].[Zn].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]>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:26])=[C:8]2[C:15]([Cl:16])=[C:14]([Cl:17])[N:13]([CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:9]2=[C:10]([C:28]#[N:30])[N:11]=1)=[O:5])[CH3:2]

Participants

7

Reactant 2

HCID 31374DimethylacetamideHCID 87451628HCID 87451628, compound

Product 1

HCID 68427635HCID 68427635, compound

Reagents, catalysts & solvents 4

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

Procedure

Prepared in analogy to that of Example 111(a) from 2,3,7-trichloro-4-hydroxy-1-phenethyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester, Zn(CN)2, Zn dust, Pd2(dba)3, and dppf in DMA. The title compound, ESI MS (m/z): 404 (M+H)+.

Sources & evidence

ORD record
ord-15b2a790905f4e1e9f4587459c7a1cd1
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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