Dimethylformamide → 3-(5-Formylpyridin-3-ylethynyl)-benzonitrile

HRID 606871Notes

Reaction equation

HRID 606871 reaction equation
C([Mg]Cl)(C)C.Br[C:7]1[CH:8]=[C:9]([C:13]#[C:14][C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=2)[C:18]#[N:19])[CH:10]=[N:11][CH:12]=1.CN(C)[CH:25]=[O:26]>O1CCCC1.C(OCC)(=O)C>[CH:25]([C:7]1[CH:8]=[C:9]([C:13]#[C:14][C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=2)[C:18]#[N:19])[CH:10]=[N:11][CH:12]=1)=[O:26]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 670476833-(5-Bromopyridin-3-ylethynyl)-benzonitrileHCID 178418918HCID 178418918, compound

Product 1

HCID 860764563-(5-Formylpyridin-3-ylethynyl)-benzonitrileYield 37%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Add a 2 M solution of isopropylmagnesium chloride in tetrahydrofuran (220 mg, 2.12 mmol) to a −20° C. solution of 3-(5-bromopyridin-3-ylethynyl)-benzonitrile, (prepared essentially as described in PREPARATION 19), (300 mg, 1.06 mmol) in tetrahydrofuran (2 mL) and stir for 1 h. Add N,N-dimethylformamide (150 mg, 2.12 mmol) in one portion, warm to room temperature, dilute with ethyl acetate and an aqueous saturated solution of sodium bicarbonate and separate the layers. Dry (magnesium sulfate), filter and concentrate. Purify by silica gel chromatography, eluting with 0:100 to 60:40 tetrahydrofuran:hexanes to give the title compound (92 mg, 37%).

Workup

  1. custom(prepared essentially
  2. customan aqueous saturated solution of sodium bicarbonate and separate the layers
  3. dry with materialDry (magnesium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify by silica gel chromatography
  7. washeluting with 0:100 to 60:40 tetrahydrofuran

Sources & evidence

ORD record
ord-d59f1afb27e642a78fabd856a441026f
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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