Ethanol → 2-Cyclohex-1-enyl-4-[2-(morpholine-4-sulfonyl)-ethyl]-phenylamine

HRID 1190127Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][S:10]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)(=[O:12])=[O:11])[CH:5]=[CH:4][C:3]=1[NH2:19].CCO.C([O-])([O-])=O.[Na+].[Na+].[C:29]1(B(O)O)[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]=1>C1(C)C=CC=CC=1.CCOC(C)=O.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>[C:29]1([C:2]2[CH:7]=[C:6]([CH2:8][CH2:9][S:10]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)(=[O:12])=[O:11])[CH:5]=[CH:4][C:3]=2[NH2:19])[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 133 mg (0.381 mmol) of 2-bromo-4-[2-(morpholine-4-sulfonyl)-ethyl]-phenylamine (as prepared in the previous step) in toluene (6 mL) and EtOH (3 mL) was treated with 1.52 mL (3.05 mmol) of 2.0 M aqueous Na2CO3 and 60.0 mg (0.476 mmol) of cyclohex-1-enylboronic acid. The mixture was degassed via sonication, placed under Ar, treated with 30.8 mg (0.027 mmol) of Pd(PPh3)4, and heated to 80° C. for 2.5 h. The mixture was cooled to RT, diluted with EtOAc (20 mL), and washed with saturated aqueous NaHCO3 (1×15 mL) and brine (1×15 mL). The organic layer was dried (MgSO4) and concentrated in vacuo to afford 132 mg (99%) of the title compound as a tan solid: Mass spectrum (ESI, m/z): Calcd. for C18H26N2O3S, 351.2 (M+H). found 351.1.

Workup

customThe mixture was degassed via sonication
temperatureThe mixture was cooled to RT
washwashed with saturated aqueous NaHCO3 (1×15 mL) and brine (1×15 mL)
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-fe0d420b0a364b92ab0ed83f50f3e921
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674100B2

Reaction notes

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