1-(1-Ethylpiperazin-4-yl)-3-bromoisoquinoline → HCID 22502478, compound

HRID 1006981Notes

Reaction equation

HRID 1006981 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH2:15][CH2:16][CH2:17][O:18][CH3:19])(=[O:14])=[O:13])=[CH:8][CH:7]=1)CCC.Br[C:29]1[N:30]=[C:31]([N:39]2[CH2:44][CH2:43][N:42]([CH2:45][CH3:46])[CH2:41][CH2:40]2)[C:32]2[C:37]([CH:38]=1)=[CH:36][CH:35]=[CH:34][CH:33]=2>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C.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>[CH2:45]([N:42]1[CH2:41][CH2:40][N:39]([C:31]2[C:32]3[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:38]=[C:29]([C:6]3[CH:7]=[CH:8][C:9]([S:12]([CH2:15][CH2:16][CH2:17][O:18][CH3:19])(=[O:13])=[O:14])=[CH:10][CH:11]=3)[N:30]=2)[CH2:44][CH2:43]1)[CH3:46]

Participants

6

Reactant 2

HCID 225024471-(1-Ethylpiperazin-4-yl)-3-bromoisoquinolineHCID 22503474HCID 22503474, compound

Product 1

HCID 22502478HCID 22502478, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 7237O-XyleneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(4-Tributylstannylphenyl) (3-methoxypropyl)sulfone (1.70 g) and 3-bromo-1-(4-ethylpiperazin-1-yl)isoquinoline (0.93 g) were heated under reflux in the presence of tetrakistriphenylphosphinepalladium(0) (0.20 g) in xylene in nitrogen atmosphere for 1 day. After cooling, the reaction solution was diluted with ethyl acetate and filtered. The filtrate was extracted with 2N hydrochloric acid, and the resulting aqueous layer was washed with ethyl acetate and adjusted to pH 10 with a 8N aqueous solution of sodium hydroxide, which was then extracted with ethyl acetate, washed with a 10% aqueous solution of sodium carbonate and brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol system), to give 0.87 g of the free compound of the title compound as a pale brown amorphous.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered
  3. extractionThe filtrate was extracted with 2N hydrochloric acid
  4. washthe resulting aqueous layer was washed with ethyl acetate
  5. extractionwas then extracted with ethyl acetate
  6. washwashed with a 10% aqueous solution of sodium carbonate and brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol system)

Sources & evidence

ORD record
ord-e3aa3272f8994abbb7c186c315a26fdc
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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