Ethyl Acrylate → HCID 89843276, compound

HRID 1050735Notes

Reaction equation

HRID 1050735 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[N:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:5]2=[O:19].[B-](F)(F)(F)F.CC([PH+](C(C)(C)C)C(C)(C)C)(C)C.[C:38]([O:42][CH2:43][CH3:44])(=[O:41])[CH:39]=[CH2:40].N(C)(C1CCCCC1)C1CCCCC1>CN(C=O)C.C(OCC)(=O)C.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC(O)=O.CC(O)=O.[Pd].[Pd]>[CH3:12][C:7]1[N:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5](=[O:19])[C:4]2[C:9](=[CH:10][CH:11]=[C:2](/[CH:40]=[CH:39]/[C:38]([O:42][CH2:43][CH3:44])=[O:41])[CH:3]=2)[N:8]=1

Participants

8

Reactant 4

HCID 8821Ethyl AcrylateHCID 24210N-Methyl dicyclohexylamineHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 21209133HCID 21209133, compound

Product 1

HCID 89843276HCID 89843276, compound

Reagents, catalysts & solvents 3

HCID 11104995trans-Bis(acetato)bis[2-[bis(2-methylphenyl)phosphino]benzyl]dipalladium(II)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The target solid of step 1 (4 g, 14.78 mmol), Herrmann's palladacycle (0.277 g, 0.30 mmol), and [(t-Bu)3Ph]BF4 (0.171 g, 0.60 mmol) mixed in DMF (40 mL) was added with ethyl acrylate (1.58 mL, 14.76 mmol) and Cy2NMe (3.27 mL, 14.78 mmol) and irradiated with microwave at 150° C. for 30 min (two times). The resulting mixture was evaporated to get dark green residue. The residue was suspended in ethyl acetate (50 mL) and washed with water (3×50 mL). The organic layer dried over MgSO4 was evaporated to get crude yellow solid of target compound of step 2. The yellow solid was put to step 3 without further purification.

Workup

  1. customirradiated with microwave at 150° C. for 30 min (two times)
  2. customThe resulting mixture was evaporated
  3. customto get dark green residue
  4. washwashed with water (3×50 mL)
  5. dry with materialThe organic layer dried over MgSO4
  6. customwas evaporated

Sources & evidence

ORD record
ord-fb05527547874d209474c073a2b4aca3
Source dataset
uspto-grants-2016_07
Patent number
US09387209B2

Reaction notes

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