Morpholine → HCID 71075618, compound

HRID 2170658Notes

Reaction equation

HRID 2170658 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:23]([O:26][C@@H:27]([CH3:32])[C:28]([O:30][CH3:31])=[O:29])=[CH:22][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([O:16]CC=C)=[O:15])=[CH:11][CH:12]=2)[C:7]([CH3:20])=[C:6]1[CH3:21].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>[Cl:1][C:2]1[CH:25]=[CH:24][C:23]([O:26][C@@H:27]([CH3:32])[C:28]([O:30][CH3:31])=[O:29])=[CH:22][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([OH:16])=[O:15])=[CH:11][CH:12]=2)[C:7]([CH3:20])=[C:6]1[CH3:21]

Participants

5

Reactant 2

HCID 8083MorpholineHCID 86674586HCID 86674586, compound

Product 1

HCID 71075618HCID 71075618, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-allyl 1-(2-chloro-5-((1-methoxy-1-oxopropan-2-yl)oxy)benzyl)-2,3-dimethyl-1H-indole-5-carboxylate (0.327 g, 0.72 mmol) and morpholine (0.63 mL, 7.2 mmol) in anhydrous THF (10 mL) was degassed, then Pd(PPh3)4 (0.083 g, 0.072 mmol) was added under argon protection. The reaction mixture was stirred at rt for 1 h. The solvent was removed and the resulting crude was dissolved in MeOH. The mixture was acidified with 2 N HCl to pH 3. The mixture was filtered and the solid was washed with water. The solid was dried for the next Step with no further purification. ESI-MS (m/z): 416 [M+1]+.

Workup

  1. customThe solvent was removed
  2. dissolutionthe resulting crude was dissolved in MeOH
  3. filtrationThe mixture was filtered
  4. washthe solid was washed with water
  5. customThe solid was dried for the next Step with no further purification

Sources & evidence

ORD record
ord-27fda3059f2d4bcfa770adf2b84831c8
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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