Sodium Carbonate → 2-[4-Amino-3-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-ethanesulfonic acid dimethylamide

HRID 1190139Notes

Reaction equation

HRID 1190139 reaction equation
[CH3:1][N:2]([CH3:16])[S:3]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[C:10](Br)[CH:9]=1)(=[O:5])=[O:4].C([O-])([O-])=O.[Na+].[Na+].[CH3:23][C:24]1([CH3:39])[CH2:29][CH2:28][C:27](B2OC(C)(C)C(C)(C)O2)=[CH:26][CH2:25]1>C1(C)C=CC=CC=1.CCO.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>[CH3:1][N:2]([CH3:16])[S:3]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[C:10]([C:27]2[CH2:28][CH2:29][C:24]([CH3:39])([CH3:23])[CH2:25][CH:26]=2)[CH:9]=1)(=[O:5])=[O:4]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 231420132-(4,4-Dimethylcyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 589943492-(4-Amino-3-bromo-phenyl)-ethanesulfonic acid dimethylamide

Product 1

HCID 589945262-[4-Amino-3-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-ethanesulfonic acid dimethylamideYield 41.2%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 477 mg (1.55 mmol) of 2-(4-amino-3-bromo-phenyl)-ethanesulfonic acid dimethylamide (as prepared in Example 28, step (c)) in toluene (13 mL) and EtOH (6.5 mL) was treated with 6.21 mL (12.4 mmol) of 2.0 M aqueous Na2CO3 and 403 mg (1.71 mmol) of 2-(4,4-dimethyl-cyclohex-1-enyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane. The mixture was degassed via sonication, placed under Ar, treated with 179 mg (0.155 mmol) of Pd(PPh3)4 and heated to 80° C. for 18 h. The mixture was cooled to RT, diluted with EtOAc (50 mL) and washed with water (1×50 mL). The aqueous layer was extracted with EtOAc (1×50 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo. Silica gel chromatography of the residue on a 50-g Varian MegaBond Elut SPE column with 50% EtOAc-hexane afforded 215 mg (41%) of the title compound as a white solid: Mass spectrum (ESI, m/z): Calcd. for C18H28N2O2S, 337.2 (M+H). found 337.1.

Workup

  1. customThe mixture was degassed via sonication
  2. temperatureThe mixture was cooled to RT
  3. washwashed with water (1×50 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (1×50 mL)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3be8a26a2f824d13bfc06d620da28e27
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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