Dimethylformamide → HCID 23074614, compound

HRID 730409Notes

Reaction equation

HRID 730409 reaction equation
[CH:1]([N-:4][CH:5]([CH3:7])[CH3:6])([CH3:3])C.[Li+].[CH:9]1([N:19]2C3=NC=CC=C3C(C#N)=C2)[C:18]2C(=CC=CC=2)[CH2:12][CH2:11][CH2:10]1.C[N:31](C=O)C.[CH3:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41].[CH2:42]1[CH2:46][O:45][CH2:44][CH2:43]1.C(C1C=CC=CC=1)C>O1CCCC1>[CH3:12][C:11]1[CH:10]=[C:9]([CH3:18])[N:19]=[C:1]2[N:4]([CH:5]3[C:6]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[CH2:36][CH2:35][CH2:7]3)[C:43]([CH:44]=[O:45])=[C:42]([C:46]#[N:31])[C:3]=12

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 2724682Lithium diisopropylamideHCID 22742125Tetrahydrofuran heptane ethylbenzolHCID 866067911,2,3,4-tetrahydro-1-naphthyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

Product 1

HCID 23074614HCID 23074614, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A 2 M solution (10 ml) of lithium diisopropylamide in heptane-THF-ethylbenzene was added to tetrahydrofuran (20 ml) under argon atmosphere, and the mixture was cooled to −78° C. in a dry ice-acetone bath. To the resultant solution was added dropwise over 30 minutes a solution of 4,6-dimethyl-1-(1,2,3,4-tetrahydro-1-naphthyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (3.0 g, 10 mmol) in tetrahydrofuran (30 ml), and after completion of the dropwise addition, the reaction mixture was stirred at −78° C. for 30 minutes. Next, DMF (3.1 ml, 40 mmol) was added thereto, the dry ice-acetone bath was removed, and then the mixture was stirred at room temperature for 2 hours. The reaction mixture was distributed to ethyl acetate and water. The organic extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under vacuum. To the residue was added hexane, and the residue was finely crushed using a spatula. The solid material was collected by filtration and washed with hexane to give the title compound (yield (amount) 2.7 g, yield (rate) 82%).

Workup

  1. additionafter completion of the dropwise addition
  2. customthe dry ice-acetone bath was removed
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. extractionThe organic extract
  5. washwas washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under vacuum
  8. additionTo the residue was added hexane
  9. customthe residue was finely crushed
  10. filtrationThe solid material was collected by filtration
  11. washwashed with hexane

Sources & evidence

ORD record
ord-8823834f97d540f4beb8fe3de37d63a6
Source dataset
uspto-grants-2009_09
Patent number
US07582651B2

Reaction notes

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