Morpholine → 1-Acetyl-6-(4-morpholinyl)-1,2-dihydrospiro[indole-3,3'-thietane]1',1'-dioxide

HRID 1618787Notes

Reaction equation

CC(C)([O-])C.[Na+].[NH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[C:47]([N:50]1[C:63]2[C:58](=[CH:59][CH:60]=[C:61](Br)[CH:62]=2)[C:52]2([CH2:55][S:54](=[O:57])(=[O:56])[CH2:53]2)[CH2:51]1)(=[O:49])[CH3:48]>O1CCOCC1.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]>[C:47]([N:50]1[C:63]2[C:58](=[CH:59][CH:60]=[C:61]([N:7]3[CH2:12][CH2:11][O:10][CH2:9][CH2:8]3)[CH:62]=2)[C:52]2([CH2:53][S:54](=[O:56])(=[O:57])[CH2:55]2)[CH2:51]1)(=[O:49])[CH3:48]

Participants

Conditions

Temperature: 110 °C

Procedure

To a microwave vessel was added sodium tert-butoxide (0.045 g, 0.466 mmol), morpholine (0.030 mL, 0.350 mmol), XPhos, Pd2(dba)3 (0.021 g, 0.023 mmol), and 1-acetyl-6-bromo-1,2-dihydrospiro[indole-3,3′thietane]1′,1′-dioxide (0.077 g, 0.233 mmol) in 1,4-dioxane (2.3 mL). The suspension was deoxygenated with argon for 5 min and stirred at 110° C. for 90 min under microwave irradiation. The crude mixture was loaded directly onto a silica gel column (eluting with a gradient of 0-10% MeOH in DCM) to give 1-acetyl-6-(4-morpholinyl)-1,2-dihydrospiro[indole-3,3′-thietane]1′,1′-dioxide as a tan oil. Mass Spectrum (ESI) m/e=337.1 (M+1).

Workup

customThe suspension was deoxygenated with argon for 5 min
washeluting with a gradient of 0-10% MeOH in DCM)

Sources & evidence

ORD record: ord-3d73a4d3b7b54d588498e9a0d21f0c25
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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