Morpholine → HCID 71075085, compound

HRID 2170713Notes

Reaction equation

HRID 2170713 reaction equation
[CH3:1][O:2][C:3](=[O:32])[C@@H:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([N:15]2[C:23]3[C:18](=[CH:19][C:20]([C:24]([O:26]CC=C)=[O:25])=[CH:21][CH:22]=3)[C:17]([CH3:30])=[C:16]2[CH3:31])[CH3:14])=[CH:9][CH:8]=1)[CH3:5].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>[CH3:1][O:2][C:3](=[O:32])[C@@H:4]([O:6][C:7]1[CH:8]=[CH:9][C:10]([CH:13]([N:15]2[C:23]3[C:18](=[CH:19][C:20]([C:24]([OH:26])=[O:25])=[CH:21][CH:22]=3)[C:17]([CH3:30])=[C:16]2[CH3:31])[CH3:14])=[CH:11][CH:12]=1)[CH3:5]

Participants

5

Reactant 2

HCID 8083MorpholineHCID 86674596HCID 86674596, compound

Product 1

HCID 71075085HCID 71075085, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The mixture of allyl 1-(1-(4-(((S)-1-methoxy-1-oxopropan-2-yl)oxy)phenyl)ethyl)-2,3-dimethyl-1H-indole-5-carboxylate (0.55 g, 1.26 mmol) and morpholine (1.0 mL, 12.6 mmol) in THF (5 mL) was degassed and then Pd(PPh3)4 (0.15 g, 0.13 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 solvent was removed and the residue was purified by silica gel chromatography to obtain the title compound. ESI-MS (m/z): 396 [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 chromatography

Sources & evidence

ORD record
ord-0a2be60e77af4bcbbf9eff1dbb57654a
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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