Dimethylacetamide → HCID 68428087, compound

HRID 642505Notes

Reaction equation

HRID 642505 reaction equation
Br[C:2]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]2=[CH:6][N:7]=[C:8]([C:11]([NH:13][CH2:14][C:15]([OH:17])=[O:16])=[O:12])[C:9]([OH:10])=[C:4]2[CH:3]=1.C[C:26]([N:28](C)C)=O>CS(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]>[C:26]([C:2]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]2=[CH:6][N:7]=[C:8]([C:11]([NH:13][CH2:14][C:15]([OH:17])=[O:16])=[O:12])[C:9]([OH:10])=[C:4]2[CH:3]=1)#[N:28]

Participants

8

Reactant 2

HCID 31374DimethylacetamideHCID 23642278HCID 23642278, compound

Product 1

HCID 68428087HCID 68428087, compound

Reagents, catalysts & solvents 5

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of [(2-bromo-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carbonyl)-amino]-acetic acid (50 mg), Zn(CN)2 (9.0 mg), Zn dust (1.0 mg), Pd2(dba)3 (5.9 mg), dppf (7.1 mg) in DMA (1 mL) was heated to 120° C. for 60 min; then the mixture was cooled, diluted with DMSO and purified by C18 reverse phase chromatography to give the desired title compound (33 mg). The title compound, ESI MS (m/z): 337 (M+H)+.

Workup

  1. temperaturethen the mixture was cooled
  2. custompurified by C18 reverse phase chromatography

Sources & evidence

ORD record
ord-52d903334fb648c48fbcf8020d6efa44
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

Loading…