Dichloromethane → HCID 69640157, compound

HRID 2188241Notes

Reaction equation

HRID 2188241 reaction equation
[CH:1]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[Na+].Br[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1.C(Cl)Cl>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[N:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:13][C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]1=2

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 7106AcridanHCID 79732-BromopyridineHCID 23676156Sodium t-butoxide

Product 1

HCID 69640157HCID 69640157, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 10.00 g of acridan (55.2 mmol), 247.7 mg of Pd(OAc)2 (1.10 mmol), 178.6 mg of tri-t-butylphosphine (0.88 mmol), 7.95 g of sodium t-butoxide (82.7 mmol), and 6.3 mL of 2-bromopyridine (66.2 mmol) in 100 mL of dry toluene was allowed to stir under inert atmosphere for 18 h. The reaction mixture was poured into a mixture of 300 mL of CH2Cl2 and 100 g of silica gel with stirring. The mixture was filtered, and the solid material was washed with 1 L of CH2Cl2. The filtrate was concentrated in vacuo to afford a yellow oil, which was taken up in hexanes. The semi-solution was again concentrated in vacuo to afford a yellow solid. The solid was triturated in 100 mL of hexanes for several hours, filtered and dried to afford 12.50 g of N-pyridylacridan (88%).

Workup

  1. stirringwith stirring
  2. filtrationThe mixture was filtered
  3. washthe solid material was washed with 1 L of CH2Cl2
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto afford a yellow oil, which
  6. concentrationThe semi-solution was again concentrated in vacuo
  7. customto afford a yellow solid
  8. customThe solid was triturated in 100 mL of hexanes for several hours
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-279fd08450bc42b092c577cd86899a04
Source dataset
uspto-grants-2002_06
Patent number
US06410732B2

Reaction notes

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