Dimethylformamide → HCID 59462304, compound

HRID 1293231Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=1.[CH3:18][N:19](C)C=O>CCOCC.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-]#N.[Zn+2].[C-]#N>[C:18]([C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=1)#[N:19]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of tert-butyl [(1S)-1-(4-bromophenyl)ethyl]carbamate (step 1 of Example 5, 1.50 g, 5.00 mmol), tetrakis(triphenylphosphine)palladium (0) (0.58 g, 0.50 mmol), zinc cyanide (0.59 g, 5.00 mmol) and N,N-dimethylforamide (30 mL) was stirred at 80° C. for 16 h under nitrogen atmosphere. After cooling to room temperature, the mixture was diluted with ether (200 mL) and washed with water (100 mL×3). The organic layer was dried over magnesium sulfate and evaporated. The residue was purified by flush column chromatography on silica gel eluting with hexane/ethyl acetate (4:1) to afford 1.11 g (90%) of the title compounds as colorless syrup: 1H-NMR (CDCl3) δ 7.64–7.61 (2H, m), 7.41 (2H, d, J=8.3 Hz), 4.83 (2H, br.s), 1.44–1.42 (12H, m).

Workup

temperatureAfter cooling to room temperature
washwashed with water (100 mL×3)
dry with materialThe organic layer was dried over magnesium sulfate
customevaporated
customThe residue was purified
customby flush column chromatography on silica gel eluting with hexane/ethyl acetate (4:1)

Sources & evidence

ORD record: ord-e6d0305f05854781ace83cb7f372cc37
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238714B2

Reaction notes

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