Morpholine → HCID 71075337, compound

HRID 2170627Notes

Reaction equation

HRID 2170627 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH2:4][O:5][C:6]1[CH:29]=[CH:28][C:9]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20]([O:22]CC=C)=[O:21])=[CH:17][CH:18]=3)[C:13]([CH3:26])=[C:12]2[CH3:27])=[CH:8][CH:7]=1.N1CCOCC1>C1COCC1.C(OCC)(=O)C.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:30])[CH2:4][O:5][C:6]1[CH:29]=[CH:28][C:9]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH:18]=3)[C:13]([CH3:26])=[C:12]2[CH3:27])=[CH:8][CH:7]=1

Participants

6

Reactant 2

HCID 8083MorpholineHCID 86674581HCID 86674581, compound

Product 1

HCID 71075337HCID 71075337, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the allyl 1-(4-(2-methoxy-2-oxoethoxy)benzyl)-2,3-dimethyl-1H-indole-5-carboxylate (536 mg, 1.3 mmol) and morpholine (1.14 mL, 13.2 mmol) in anhydrous THF was degassed with argon. Then Pd(PPh3)4 (152 mg, 0.13 mmol) was added and the reaction stirred under argon protection for 1.5 h. The reaction mixture was diluted with ethyl acetate, washed with brine, concentrated. The title compound was precipitated in ethyl ether as a beige powder (430 mg, 89%). ESI-MS (m/z): 368 [M+H]+.

Workup

  1. washwashed with brine
  2. concentrationconcentrated
  3. customThe title compound was precipitated in ethyl ether as a beige powder (430 mg, 89%)

Sources & evidence

ORD record
ord-06f705ca21e14c64ac320f1da5723ee9
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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