Ethyl Acetate → HCID 58754886, compound

HRID 1711235Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[NH2:11].[C:12]1(B(O)O)[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>O1CCOCC1.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:12]1([C:2]2[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=2[NH2:11])[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 2-bromo-4-isopropyl-phenylamine (214 mg, 1.00 mmol), cyclohexane-1-enyl boronic acid (139 mg, 1.10 mmol) and Pd(PPh3)4 (116 mg, 0.100 mmol) in 5 mL of 1,4-dioxane was added 2.0 M aqueous Na2CO3 solution (4.0 mL, 8.0 mmol). The resulting mixture was stirred at 80° C. for 8 h under Ar, and then cooled to RT. The reaction was treated with EtOAc (20 mL) and washed with H2O (2×10 mL) and brine (10 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (DCM) to give 205 mg (95%) of the title compound as a light brown oil. Mass spectrum (ESI, m/z): Calcd. for C15H21N, 216.2 (M+H), found 216.1.

Workup

temperaturecooled to RT
washwashed with H2O (2×10 mL) and brine (10 mL)
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography on silica gel (DCM)

Sources & evidence

ORD record: ord-c0912b678511472fb35349753f87d7cc
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790724B2

Reaction notes

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