Dimethylacetamide → HCID 68426259, compound

HRID 642529Notes

Reaction equation

HRID 642529 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:24])=[C:8]2[CH:14]=[C:13](Br)[N:12]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].C[C:26]([N:28](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:24])=[C:8]2[CH:14]=[C:13]([C:26]#[N:28])[N:12]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]

Participants

7

Reactant 2

HCID 31374DimethylacetamideHCID 68429027HCID 68429027, compound

Product 1

HCID 68426259HCID 68426259, 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 mixture of 2-bromo-1-(3-fluoro-benzyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (1000 mg), Zn(CN)2 (150 mg), Zn dust (17 mg), Pd2(dba)3 (59 mg), dppf (71 mg) in DMA (8 mL) was heated to 120° C. for 90 min; then the mixture was partitioned between EtOAc and water, the organic phase was then washed with sat. NaCl solution, dried over anhydrous sodium sulfate, filtered and concentrated sequentially to give a residue, which was purified with column to give desired title compound (270 mg). The title compound, ESI MS (m/z): 340 (M+H)+.

Workup

  1. customthen the mixture was partitioned between EtOAc and water
  2. washthe organic phase was then washed with sat. NaCl solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated sequentially
  6. customto give a residue, which
  7. customwas purified with column

Sources & evidence

ORD record
ord-670252135ffd41f5a8bb79c6d43be693
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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