HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Water → 7-(3,4-dihydro-1H-isoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-5-carbaldehyde

HRID 1445113
Notes
Print preview

Reaction equation

HRID 1445113 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][N:12]1[C:21]1[N:22]=[C:23]([C:32]#N)[CH:24]=[C:25]2[C:29]([CH3:30])=[C:28]([CH3:31])[NH:27][C:26]=12.[OH2:34].[OH-].[Na+]>O1CCCC1.C(OCC)C>[CH2:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][N:12]1[C:21]1[N:22]=[C:23]([CH:32]=[O:34])[CH:24]=[C:25]2[C:29]([CH3:30])=[C:28]([CH3:31])[NH:27][C:26]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21225700DiisobutylaluminumhydrideHCID 67141782HCID 67141782, compound

Product 1

HCID 866152637-(3,4-dihydro-1H-isoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-5-carbaldehydeYield 16%

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

Diisobutyl aluminum hydride (1.0M in toluene solution; 1.98 ml, 1.98 mmol) was added at −78° C. to a solution of 7-(3,4-dihydro-1H-isoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-5-carbonitrile (300 mg, 099 mmol) prepared in Example 682 in anhydrous tetrahydrofuran (2 ml). The reaction mixture was stirred for 5 hours and then diluted with diethyl ether. Water (2 ml) and 15% sodium hydroxide solution (2 ml) were added to the reaction mixture, which was then stirred for 30 minutes. The organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/3, v/v) to give 50.6 mg of the titled compound as a white solid. (Yield: 16%).

Workup

  1. stirringwas then stirred for 30 minutes
  2. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/3

Sources & evidence

ORD record
ord-9c5de0f27fb54c14b838b764537c8a48
Source dataset
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07662832B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes