Dichloromethane → HCID 66966216, compound

HRID 1711838Notes

Reaction equation

HRID 1711838 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[NH:14][C:13](=[O:15])[C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[CH2:7][C:6]=2[CH:16]=1.[C:17]([O:21]C(C)(C)C)(=[O:20])[CH:18]=[CH2:19].C(N(C(C)C)C(C)C)C.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(Cl)[Cl:58]>C(#N)CC.CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[ClH:58].[O:15]=[C:13]1[C@H:12]2[N:8]([CH2:9][CH2:10][CH2:11]2)[CH2:7][C:6]2[CH:16]=[C:2](/[CH:19]=[CH:18]/[C:17]([OH:21])=[O:20])[CH:3]=[N:4][C:5]=2[NH:14]1

Participants

9

Reactant 5

HCID 6344DichloromethaneHCID 15458tert-Butyl acrylateHCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 57742026HCID 57742026, compound

Product 1

HCID 66966216HCID 66966216, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 7854PropionitrileSolvent

Procedure

A suspension of (S)-6-bromo-1,2,3,4,9,10a-hexahydro-3a,8,9-triaza-benzo[f]azulen-10-one (1.46 g, 5.17 mmol) in propionitrile (40 mL) and DMF (10 mL) was de-oxygenated with Ar for 30 min. The mixture was treated with tert-butyl acrylate (3.0 mL, 20 mmol) and (i-Pr)2EtN (1.9 mL, 11 mmol) and was de-oxygenated with Ar for 10 min. Pd(OAc)2 (0.12 g, 0.53 mmol) and P(o-tol)3 (0.34 mg, 1.12 mmol) were added simultaneously, and the mixture was de-oxygenated a third time for 5 min. The mixture was heated to reflux overnight then allowed to cool. The resulting precipitate was isolated by filtration, dissolved in CH2Cl2, filtered through Celite and the solvent was removed in vacuo to give the title compound (0.68 g, 40%) as an off-white solid: MS (ESI) m/e 330 (M+H)+.

Workup

  1. waitwas de-oxygenated with Ar for 10 min
  2. customfor 5 min
  3. temperatureThe mixture was heated
  4. temperatureto reflux overnight
  5. temperatureto cool
  6. customThe resulting precipitate was isolated by filtration
  7. filtrationfiltered through Celite
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a6c2c9f90b1d48509f5c594efe81da03
Source dataset
uspto-grants-2010_09
Patent number
US07790709B2

Reaction notes

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