Dimethylformamide → HCID 69519861, compound

HRID 1178785Notes

Reaction equation

HRID 1178785 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14](Br)=[CH:15][CH:16]=2)[CH2:11][C@H:10]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:22])=[O:21])[C:9]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:30][N:31](C=O)C>CO.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C-]#N.[C-]#N.[Zn+2]>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:30]#[N:31])=[CH:15][CH:16]=2)[CH2:11][C@H:10]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:22])=[O:21])[C:9]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 6228DimethylformamideHCID 58975530HCID 58975530, compound

Product 1

HCID 69519861HCID 69519861, compound

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of Example 8 (9 mg, 0.018 mmol), tetrakis(triphenylphosphine)-palladium (22 mg, 0.019 mmol), and Zn(CN)2 (15 mg, 0.128 mmol) in DMF (1 mL) stirring under argon was heated to 120° for 1 h. After cooling to RT, the heterogeneous was diluted with a 80% MeOH in H2O solution and filtered. The filtrate was directly injected to reverse phase preparative HPLC, which provided the title compound (7 mg). HPLC/MS retention time=3.3 min (Phenomenex Luna 5 micron C18 4.6 mm×50 mm column eluted with a 0% to 100% B solvent gradient over 4 min; solvent A=90% H2O, 10% MeOH, 10 mM NH4OAc and solvent B=10% H2O, 90% MeOH, 10 mM NH4OAc; flow rate=4.0 mL/min; UV detection at 220 nm); m/z=418 [M+H]+, 416 [M−H]−.

Workup

  1. temperaturewas heated to 120° for 1 h
  2. filtrationfiltered

Sources & evidence

ORD record
ord-7573339439554ff9a03cd462a8fc5aad
Source dataset
uspto-grants-2007_10
Patent number
US07276608B2

Reaction notes

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