Morpholine → HCID 71075610, compound

HRID 2170700Notes

Reaction equation

HRID 2170700 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:27]=[CH:28][CH:29]=1)[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][C:15]([C:19]([O:21]CC=C)=[O:20])=[CH:16][CH:17]=2)[C:12]([CH3:25])=[C:11]1[CH3:26])([CH3:5])[CH3:4])#[N:2].N1CCOCC1>C1COCC1.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>[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:27]=[CH:28][CH:29]=1)[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][C:15]([C:19]([OH:21])=[O:20])=[CH:16][CH:17]=2)[C:12]([CH3:25])=[C:11]1[CH3:26])([CH3:5])[CH3:4])#[N:2]

Participants

5

Reactant 2

HCID 8083MorpholineHCID 86674589HCID 86674589, compound

Product 1

HCID 71075610HCID 71075610, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The mixture of allyl 1-(3-(2-cyanopropan-2-yl)benzyl)-2,3-dimethyl-1H-indole-5-carboxylate (0.688 g, 1.78 mmol) and morpholine (1.6 mL, 17.8 mmol) in THF (5 mL) was degassed and then Pd(PPh3)4 (0.21 g, 0.18 mmol) was added. The mixture was stirred at room temperature for 1 h. The solvent was removed and the residue was dissolved in Methanol and acidified to pH4. The solvent was removed and the residue was purified by silica gel to obtain the title compound. ESI-MS (m/z): 347 [M+H]+.

Workup

  1. customwas degassed
  2. customThe solvent was removed
  3. dissolutionthe residue was dissolved in Methanol
  4. customThe solvent was removed
  5. customthe residue was purified by silica gel

Sources & evidence

ORD record
ord-44b3877c85414afba2a9b233191fd665
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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