Diethyl Ether → HCID 20277029, compound

HRID 1248616Notes

Reaction equation

HRID 1248616 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.[Li+].[CH3:10]CC[CH2-].C[C:15]1[CH:16]=[C:17]([CH:21]2[CH2:29][C:28]3[C:23](=[CH:24][CH:25]=C[CH:27]=3)[C:22]2=O)[CH:18]=NC=1.[NH4+:31].[Cl-].CC[O:35][CH2:36][CH3:37]>O>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:36]2([OH:35])[C:37]3[C:29](=[CH:21][C:17]([CH3:18])=[CH:16][CH:15]=3)[CH:28]([C:23]3[CH:22]=[CH:10][N:31]=[CH:25][CH:24]=3)[CH2:27]2)=[CH:3][CH:4]=1

Participants

7

Reactant 5

HCID 3283Diethyl Ether2×HCID 99931-Bromo-4-fluorobenzeneHCID 25517Ammonium ChlorideHCID 61028n-Butyl lithiumHCID 70412704HCID 70412704, compound

Product 1

HCID 20277029HCID 20277029, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-20 °C

Procedure

4-Bromofluorobenzene (87.5 g) dissolved in 1000 ml of dry ether was cooled to -20° C. and kept under dry N2.N-butyllithium (0.5 moles 15% W/V in n-hexane) was added during 1 hour while the temperature was kept below 0° C. The reaction mixture was stirred for another 1/2 h and further cooled to -30° C. 5-Methyl-3-pyridylindanone (75 g) (prepared according to the standard methods--J. Med. Chem., 11, (1968), 1064-1066) dissoled in dry ether (500 ml) was added dropwise at such a rate as to keep the temperature below -10° C. Subsequently the temperature was slowly raised to room temperature and the mixture poured into NH4Cl(100 g) in H2O (3 liters). The organic phase was separated and washed with brine, dried (MgSO4), and the solvents evaporated. Upon addition of ether (200 ml) the title compound precipitated and was filtered off. Yield: 55 g (52%). MP: 187°-192° C.

Workup

  1. customwas kept below 0° C
  2. temperaturefurther cooled to -30° C
  3. additionwas added dropwise at such a rate as
  4. customthe temperature below -10° C
  5. temperatureSubsequently the temperature was slowly raised to room temperature
  6. customThe organic phase was separated
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. customthe solvents evaporated
  10. additionUpon addition of ether (200 ml) the title compound
  11. customprecipitated
  12. filtrationwas filtered off

Sources & evidence

ORD record
ord-6a0de7983d4040babc1cfaf93e3a5b08
Source dataset
uspto-grants-1985_06
Patent number
US04525360

Reaction notes

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