HCID 86607519, compound → HCID 67233363, compound

HRID 1465970Notes

Reaction equation

HRID 1465970 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:13]=[C:12](Br)[C:11]2[CH:15]=[CH:16][S:17][C:10]=2[C:9]=1[OH:18])=[O:7])[CH2:2][CH2:3][CH3:4].[C:19]([Cu])#[N:20]>[C-]#N.C([N+](CC)(CC)CC)C.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].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O1CCOCC1>[CH2:1]([O:5][C:6]([C:8]1[N:13]=[C:12]([C:19]#[N:20])[C:11]2[CH:15]=[CH:16][S:17][C:10]=2[C:9]=1[OH:18])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 2

HCID 86607519HCID 86607519, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 67233363HCID 67233363, compoundYield 151.3%

Reagents, catalysts & solvents 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 3014735Tetraethylammonium cyanideCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4-bromo-7-hydroxy-thieno[3,2-c]pyridine-6-carboxylic acid butyl ester (example 44a, 165 mg, 0.5 mmol), CuCN (181 mg, 2 mmol), tris(dibenzylideneacetone)dipalladium(0) (46 mg, 0.05 mmol), 1,1′-bis(diphenylphosphino)ferrocene (114 mg, 0.2 mmol), tetraethylammonium cyanide (83 mg, 0.5 mmol), and anhydrous 1,4-dioxane (3 ml) was heated in a microwave oven at 140° C. with stirring for 15 min. Then silica gel was added and the mixture concentrated in vacuo. The residue was added on top of a short column filled with silica gel. Elution with ethyl acetate:hexanes=1:1 and in vacuo concentration gave a tan solid (209 mg). Purification by flash column chromatography on silica gel using ethyl acetate:hexanes=3:7 and then 1:1 gave the title compound as a tan solid (63 mg); MS-(+)-ion: MS-(−)-ion: M−1=275.1.

Workup

  1. additionThen silica gel was added
  2. concentrationthe mixture concentrated in vacuo
  3. additionThe residue was added on top of a short column
  4. additionfilled with silica gel
  5. washElution with ethyl acetate
  6. concentrationhexanes=1:1 and in vacuo concentration

Sources & evidence

ORD record
ord-08c9d89ae5bb4326be9e4aa93bd9e104
Source dataset
uspto-grants-2015_04
Patent number
US09000006B2

Reaction notes

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