Dimethylformamide → HCID 71743885, compound

HRID 2283513Notes

Reaction equation

HRID 2283513 reaction equation
Br[C:2]1[C:8]([F:9])=[CH:7][C:5]([NH2:6])=[C:4]([O:10][CH3:11])[CH:3]=1.[CH3:12][N:13](C1C(C2C(P(C3CCCCC3)C3CCCCC3)=CC=CC=2)=CC=CC=1)C.CN(C=O)C>O.[C-]#N.[Zn+2].[C-]#N.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]>[NH2:6][C:5]1[C:4]([O:10][CH3:11])=[CH:3][C:2]([C:12]#[N:13])=[C:8]([F:9])[CH:7]=1

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 223472984-Bromo-5-fluoro-2-methoxyaniline

Product 1

HCID 71743885HCID 71743885, compoundYield 492.4%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a pressure tube was added 4-bromo-5-fluoro-2-methoxyaniline (0.24 g, 1.1 mmol), zinc cyanide (0.10 g, 0.87 mmol), Pd2(dba)3 (100 mg, 0.11 mmol), DavePhos (86 mg, 0.22 mmol) and DMF (3 mL). The reaction was sealed and stirred at 100° C. for 6 hours. The reaction was diluted with water and extracted with EtOAc. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography to give 4-amino-2-fluoro-5-methoxybenzonitrile (0.18 g, 77%).

Workup

  1. customThe reaction was sealed
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-4af533ec264f451b83bc778ff4333a2e
Source dataset
uspto-grants-2015_09
Patent number
US09145402B2

Reaction notes

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