Morpholine → HCID 67284857, compound

HRID 1618757Notes

Reaction equation

HRID 1618757 reaction equation
Br[C:2]1[CH:7]=[C:6]2[N:8]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:9][C:10]3([CH2:15][CH2:14][S:13](=[O:17])(=[O:16])[CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.CC(C)([O-])C.[Na+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:25]1([C:2]2[CH:7]=[C:6]3[N:8]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:9][C:10]4([CH2:15][CH2:14][S:13](=[O:17])(=[O:16])[CH2:12][CH2:11]4)[C:5]3=[CH:4][CH:3]=2)[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 67285855HCID 67285855, compound

Product 1

HCID 67284857HCID 67284857, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to procedure N by stirring tert-butyl 6-bromo-2′,3′,5′,6′-tetrahydrospiro[indole-3,4′-thiopyran]-1(2H)-carboxylate 1′,1′-dioxide (200 mg, 0.48 mmol), morpholine (62.8 μL, 0.721 mmol), sodium tert-butoxide, Pd2dba3 (44 mg, 0.048 mmol) and XPhos (45.8 mg, 0.096 mmol) in toluene (6 mL) at 100° C. for 2 h. Purification by column chromatography (hexanes:EtOAc, 1:0 to 1:1 as eluant) gave tert-butyl 6-(4-morpholinyl)-2′,3′,5′,6′-tetrahydrospiro[indole-3,4′-thiopyran]-1(2H)-carboxylate 1′,1′-dioxide. Mass Spectrum (ESI) m/e=423.0 (M+1).

Workup

  1. customPrepared
  2. customPurification by column chromatography (hexanes:EtOAc, 1:0 to 1:1 as eluant)

Sources & evidence

ORD record
ord-0220583699da4aebbaebb8f55a5d65bc
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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