Triethylamine → HCID 66920803, compound

HRID 1364566Notes

Reaction equation

HRID 1364566 reaction equation
[CH3:1][S:2]([C:5]1[CH:25]=[CH:24][C:8]([CH2:9][NH:10][C:11]([C:13]2[CH:18]=[C:17](I)[C:16]([Cl:20])=[C:15]([O:21][CH2:22][CH3:23])[N:14]=2)=[O:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(OC(C)(C)C)(=O)C=C.C(N(CC)CC)C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:20][C:16]1[CH:17]=[CH:18][C:13]([C:11]([NH:10][CH2:9][C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:25][CH:24]=2)=[O:12])=[N:14][C:15]=1[O:21][CH2:22][CH3:23]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 66920991HCID 66920991, compound

Product 1

HCID 66920803HCID 66920803, compoundYield 10.8%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

This material obtained from step A (50 mg, 0.1 mmol) was dissolved in N,N-dimethylformamide (0.1 mL) followed by addition of t-butyl acrylate (25 mg, 0.2 mmol), (Tol)3P (6 mg, 0.02 mmol), palladium(II) acetate (2 mg, 0.01 mmol), and triethylamine (20 mg, 0.2 mmol). The mixture was heated to 100° C. for 2 h, cooled to room temperature, and partitioned between ethyl acetate and water. The organic layer was washed with brine, drived over Na2SO4, filtered and evaporated in vacuo. The residue was purified by silica gel flash chromatography eluting with 100% ethyl acetate to provide the title compound (4 mg, 10%). 1H NMR (500 MHz, DMSO-d6) δ 9.29 (t, J=6.0 Hz, 1H), 8.05 (d, J=7.5 Hz, 1H), 7.88 (d, J=8.5 Hz, 2H), 7.61 (d, J=8.0 Hz, 1H), 7.57 (d, J=8.0 Hz, 2H), 4.60 (d, J=7.0 Hz, 2H), 4.59 (q, J=7.0 Hz, 2H), 3.18 (s, 3H), and 1.38 (d, J=7.0, 3H). MS (m/e) positive mode: 369, 71 (3:1, M+H)+.

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel flash chromatography
  7. washeluting with 100% ethyl acetate

Sources & evidence

ORD record
ord-b9899866aa4a4f6a92c5d4cd750b5935
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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