Methyl Acrylate → HCID 69219981, compound

HRID 272691Notes

Reaction equation

HRID 272691 reaction equation
Br[C:2]1[C:18]([O:19][CH3:20])=[CH:17][C:5]2[NH:6][C:7](=[O:16])[C:8]3[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:9]=3[NH:10][C:4]=2[CH:3]=1.[C:21]([O:25][CH3:26])(=[O:24])[CH:22]=[CH2:23].CCN(CC)CC>CN(C=O)C.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:15][C:12]1[CH:13]=[CH:14][C:8]2[C:7](=[O:16])[NH:6][C:5]3[CH:17]=[C:18]([O:19][CH3:20])[C:2]([CH:23]=[CH:22][C:21]([O:25][CH3:26])=[O:24])=[CH:3][C:4]=3[NH:10][C:9]=2[CH:11]=1

Participants

7

Reactant 3

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 69218675HCID 69218675, compound

Product 1

HCID 69219981HCID 69219981, compoundYield 83.6%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 223G (71 mg, 0.2 mmol), methyl acrylate (64 mg, 0.8 mmol), Pd(dppf)Cl2 (33 mg, 0.04 mmol) and 1 mL Et3N in 3 mL of DMF was heated at 110° C. overnight. The reaction mixture was diluted with EtOAc when it was still warm, and poured onto water. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated. The residue was triturated with 20 mL of 1:1 EtOH/Aceton to give 60 mg of the title compound. MS (DCI) m/e 359 (M+H)+; 1H NMR (500 MHz, DMSO-d6) δ 10.04 (s, 1H), 7.91 (s, 1H), 7.86-7.75 (m, 2H), 7.25 (s, 1H), 7.03 (d, J=1.53 Hz, 1H), 6.93 (dd, J=8.59, 1.84 Hz, 1H), 6.75 (s, 1H), 6.35 (d, J=15.96 Hz, 1H), 3.78 (s, 3H), 3.77 (s, 3H).

Workup

  1. temperaturewas still warm
  2. additionpoured onto water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was triturated with 20 mL of 1:1 EtOH/Aceton

Sources & evidence

ORD record
ord-1940dfcf23ce43b6a845090ac639e9a5
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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