Morpholine → HCID 71075333, compound

HRID 2170718Notes

Reaction equation

HRID 2170718 reaction equation
[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH:27]=[CH:28][CH:29]=2)[CH2:9][N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]([O:21]CC=C)=[O:20])=[CH:16][CH:17]=3)[C:12]([CH3:25])=[C:11]2[CH3:26])[CH2:5][CH2:4]1)#[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]1([C:6]2[CH:7]=[C:8]([CH:27]=[CH:28][CH:29]=2)[CH2:9][N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]([OH:21])=[O:20])=[CH:16][CH:17]=3)[C:12]([CH3:25])=[C:11]2[CH3:26])[CH2:4][CH2:5]1)#[N:2]

Participants

5

Reactant 2

HCID 8083MorpholineHCID 86674597HCID 86674597, compound

Product 1

HCID 71075333HCID 71075333, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The mixture of allyl 1-(3-(1-cyanocyclopropyl)benzyl)-2,3-dimethyl-1H-indole-5-carboxylate (375 mg, 0.98 mmol) and morpholine (0.8 mL, 9.2 mmol) in THF (8 mL) was degassed and then Pd(PPh3)4 (117 mg, 0.10 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 pH 4. The precipitate was collected and washed with water to obtain the title compound.

Workup

  1. customwas degassed
  2. customThe solvent was removed
  3. dissolutionthe residue was dissolved in Methanol
  4. customThe precipitate was collected
  5. washwashed with water

Sources & evidence

ORD record
ord-8b5f423b20cb43888807304be023fde7
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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