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Dimethylformamide → HCID 67290985, compound

HRID 511824
Notes
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Reaction equation

HRID 511824 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])=[CH:4][N:3]=1.C(=O)(O)[O-].[Na+].[CH3:22][N:23](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:22]#[N:23])=[N:3][CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 59596668HCID 59596668, compound

Product 1

HCID 67290985HCID 67290985, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst
HCID 178418397
HCID 178418397, compound
Catalyst

Conditions

Temperature
60 °C

Procedure

To a mixture of 2-bromo-5-(2-fluorobenzyloxy)pyridine (1.5 g, 5.3 mmol) and zinc cyanide (0.81 g, 6.9 mmol) in DMF (20 mL) was added Tetrakis(triphenylphosphine)palladium(0) (0.61 g, 0.53 mmol) at room temperature. After being stirred at 60° C. for 4 hours, sat. sodium bicarbonate aqueous solution was added to the mixture. The mixture was filtered off through a pad of Celite. The filtrate was extracted with ethyl acetate, dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (2:1 (v/v)) to give 0.69 g (57% yield) of the title compound as a light yellow solid:

Workup

  1. filtrationThe mixture was filtered off through a pad of Celite
  2. extractionThe filtrate was extracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (2:1 (v/v))

Sources & evidence

ORD record
ord-3764e2398f124233a6f36f7c933d5788
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09101616B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes