Cesium carbonate → HCID 71080464, compound

HRID 593310Notes

Reaction equation

HRID 593310 reaction equation
[CH2:1]([C@@:3]1([CH2:22][C:23]([O:25][CH2:26]C)=[O:24])[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8](OS(C(F)(F)F)(=O)=O)[CH:9]=2)[C:4]1=[O:21])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[F:34][C:35]1[CH:36]=[C:37]([NH:42][C:43]([NH:45][C:46]2[CH:51]=[CH:50][C:49](B3OC(C)(C)C(C)(C)O3)=[CH:48][CH:47]=2)=[O:44])[CH:38]=[CH:39][C:40]=1[F:41]>O1CCOCC1.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>[F:34][C:35]1[CH:36]=[C:37]([NH:42][C:43](=[O:44])[NH:45][C:46]2[CH:47]=[CH:48][C:49]([C:8]3[CH:9]=[C:10]4[C:5](=[CH:6][CH:7]=3)[C:4](=[O:21])[C@@:3]([CH2:22][C:23]([O:25][CH3:26])=[O:24])([CH2:1][CH3:2])[CH2:12][CH2:11]4)=[CH:50][CH:51]=2)[CH:38]=[CH:39][C:40]=1[F:41]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 123261411HCID 123261411, compoundHCID 123627605HCID 123627605, compound

Product 1

HCID 71080464HCID 71080464, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

Pd(PPh3)4 (0.018 g, 0.015 mmol) was added to a solution of (S)-ethyl 2-(2-ethyl-1-oxo-6-(trifluoromethylsulfonyloxy)-1,2,3,4-tetrahydronaphthalen-2-yl)acetate (129C, 0.3 g, 0.761 mmol) in 10 mL 1,4 dioxane-H2O (4:1) mixture under argon atmosphere, followed by cesium carbonate (0.74 g, 2.28 mmol) and Example 217B (0.313 g, 0.837 mmol). The reaction mixture was degassed for 30 min. The reaction mixture was refluxed for 12 h, and solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic layer was separated, dried over Na2SO4, filtered and concentrated under reduced pressure. The product was purified by flash chromatography using 20% ethyl acetate in hexane to afford title compound (0.15 g, 40%) as solid. 1H NMR (400 MHz, CDCl3): δ 8.05 (s, 1H), 8.03 (s, 1H), 7.44-7.37 (m, 3H), 7.35-7.31 (m, 4H), 7.18 (m, 1H), 7.08-6.97 (m, 2H), 3.67 (s, 3H), 3.14 (m, 1H), 3.04 (d, J=16 Hz, 1H), 2.90 (m, 1H), 2.5 (d, J=16 Hz, 1H), 2.45 (m, 1H), 2.05 (m, 1H), 1.79-1.6 (m, 2H), 0.94 (t, J=7.6 Hz, 3H); ESI-MS m/z=493 (M+H)+.

Workup

  1. customThe reaction mixture was degassed for 30 min
  2. temperatureThe reaction mixture was refluxed for 12 h
  3. customsolvent was removed under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and water
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-854dbe9a95d141a496d4f2401670f9ee
Source dataset
uspto-grants-2016_01
Patent number
US09242929B2

Reaction notes

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