Pyridine → HCID 58670306, compound

HRID 900820Notes

Reaction equation

HRID 900820 reaction equation
[C:1]([C:3]12[CH2:18][C:17]([CH3:22])([C:19](O)=[O:20])[CH:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=31)[C:9]1[C:4]2=[CH:5][CH:6]=[CH:7][CH:8]=1)#[N:2].N1C=CC=CC=1.N1C(F)=NC(F)=NC=1[F:31]>C(Cl)Cl.Cl>[C:1]([C:3]12[CH2:18][C:17]([CH3:22])([C:19]([F:31])=[O:20])[CH:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=31)[C:9]1[C:4]2=[CH:5][CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 23595949HCID 23595949, compound

Product 1

HCID 58670306HCID 58670306, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 9-cyano-9,10-dihydro-11-methyl-9,10-ethanoanthracene-11-carboxylic acid (hereafter called Core A) (5.26 g, 18.2 mmol) and pyridine (2.2 mL, 27.0 mmol) in 10 mL of DCM was added a solution of cyanuric fluoride (2.14 g, 27.0 mmol) dropwise. After stirring 30 min, the reaction was diluted with 1N HCl, and extracted 2×DCM. The DCM extracts were dried over MgSO4. The solution was filtered, concentrated by rotary evaporator to give 4.8 g (91%) of 9-cyano-9,10-dihydro-11-methyl-9,10-ethano-anthracene-11-carboxylic acid fluoride, Core B. MS found: (M+H)+=292.

Workup

  1. extractionextracted 2×DCM
  2. dry with materialThe DCM extracts were dried over MgSO4
  3. filtrationThe solution was filtered
  4. concentrationconcentrated by rotary evaporator

Sources & evidence

ORD record
ord-afda64dc98624aa6968b963699fd3167
Source dataset
uspto-grants-2008_04
Patent number
US07361654B2

Reaction notes

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