Dimethylformamide → HCID 66864796, compound

HRID 1615844Notes

Reaction equation

HRID 1615844 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][C:19]=1I)[CH2:16][C@:6]1([C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]1=[O:15])[CH2:5]2.[CH3:21][N:22](C=O)C>O.[Zn].[C-]#N.[Zn+2].[C-]#N.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[NH2:1][C:2]1[CH:3]=[C:4]2[C:17]([CH2:16][C@@:6]3([CH2:5]2)[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]3=[O:15])=[CH:18][C:19]=1[C:21]#[N:22]

Participants

7

Reactant 2

HCID 6228DimethylformamideHCID 58118705HCID 58118705, compound

Product 1

HCID 66864796HCID 66864796, compound

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 178418851HCID 178418851, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of (2S)-5-amino-6-iodo-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one from Step A (750 mg, 1.99 mmol), zinc dust (15.6 mg, 0.24 mmol) and zinc cyanide (467 mg, 3.98 mmol) in DMF (3.4 mL) at ambient temperature was added bis(tri-t-butylphosphine)palladium (102 mg, 0.199 mmol). The reaction mixture was heated at 80° C. for 2 h, diluted with H2O, and extracted with EtOAc (3×). The combined organic layers were filtered through a plug of Celite, dried over MgSO4, filtered, and concentrated in vacuo. The oily residue was purified by silica gel chromatography, eluting with EtOAc:hexanes—80:20, to afford the title compound. MS: m/z=277 (M+1).

Workup

  1. extractionextracted with EtOAc (3×)
  2. filtrationThe combined organic layers were filtered through a plug of Celite
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe oily residue was purified by silica gel chromatography
  7. washeluting with EtOAc

Sources & evidence

ORD record
ord-097854d72888494ab637a5322dd8dd9f
Source dataset
uspto-grants-2014_07
Patent number
US08765759B2

Reaction notes

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