Water → HCID 13799194, compound

HRID 2413717Notes

Reaction equation

HRID 2413717 reaction equation
Br[C:2]#[C:3][C:4]1[N:5]=[CH:6][C:7]2[NH:8][C:9]3[C:14]([C:15]=2[C:16]=1[CH2:17][O:18][CH3:19])=[C:13]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:12]=[CH:11][CH:10]=3.O1CCCC1.C([Li])(C)(C)C.O>CCCCC>[CH2:21]([O:20][C:13]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:14]=1[C:15]1[C:16]([CH2:17][O:18][CH3:19])=[C:4]([C:3]#[CH:2])[N:5]=[CH:6][C:7]=1[NH:8]2)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 13799193HCID 13799193, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 13799194HCID 13799194, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 0.164 g of 1-bromo-2-(5-benzyloxy-4-methoxymethyl-beta-carbolin-3-yl)acetylene in 5 ml of abs. tetrahydrofuran is cooled under N2 atmosphere to -78° C. and mixed with 0.46 ml of a 1.4 molar solution of tertbutyllithium in pentane. After 1 hour stirring at -78° C. the reaction mixture is heated to room temperature and stirred for 1.5 hours more. Then it is carefully decomposed with water and extracted with dichloromethane. The organic phases are combined, dried and the solvent evaporated. The residue is chromatographed over silica gel with acetone/hexane=1+1 as eluant. 0.056 g of 5-benzyloxy-3-ethinyl-4-methoxymethyl-beta-carboline with a melting point of 207°-209° is obtained.

Workup

  1. temperatureis heated to room temperature
  2. stirringstirred for 1.5 hours more
  3. extractionextracted with dichloromethane
  4. customdried
  5. customthe solvent evaporated
  6. customThe residue is chromatographed over silica gel with acetone/hexane=1+1 as eluant

Sources & evidence

ORD record
ord-59feee2f88c1470680d7f33d8f726e63
Source dataset
uspto-grants-1988_01
Patent number
US04719210

Reaction notes

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