Morpholine → HCID 57753496, compound

HRID 1931027Notes

Reaction equation

HRID 1931027 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][N:6]2[C:11]([C:13]1[CH:18]=[C:17]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:16]=[CH:15][C:14]=1[O:23][C@@H:24]([CH3:29])[C:25]([F:28])([F:27])[F:26])=[O:12].[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1>[CH3:22][S:19]([C:17]1[CH:16]=[CH:15][C:14]([O:23][C@@H:24]([CH3:29])[C:25]([F:27])([F:28])[F:26])=[C:13]([C:11]([N:6]2[C:7]3[C:3](=[C:2]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)[CH:10]=[CH:9][CH:8]=3)[CH2:4][CH2:5]2)=[O:12])[CH:18]=1)(=[O:20])=[O:21]

Participants

5

Reactant 3

HCID 8083Morpholine2×HCID 634876Binap, (A+-)-HCID 57753710HCID 57753710, compound

Product 1

HCID 57753496HCID 57753496, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 0.2 mmol (4-Bromo-2,3-dihydro-indol-1-yl)-[5-methanesulfonyl-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-methanone (example 211), 0.4 mmol morpholine, 0.3 mmol sodium tert-butylate, 2.5 mg rac.BINAP and 2.0 mg tris-(dibenzylidenaceton)-dipalladium chloroform complex in 5 ml toluene is heated at 80° C. for 3 hours. Fresh morpholine (0.4 mmol) is added and the mixture hold at 80° overnight. The reaction mixture is concentrated. Chromatography of the residue (silica gel; ethyl acetate/heptane) yields the title compound as a slightly yellow solid. Yield=57%. MS (m/e): 499.3 [M+H]+, 100%).

Workup

  1. customat 80°
  2. customovernight
  3. concentrationThe reaction mixture is concentrated

Sources & evidence

ORD record
ord-8779e8d417da4a4b86a43ec9c06e9884
Source dataset
uspto-grants-2012_05
Patent number
US08188139B2

Reaction notes

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