Hydrochloric Acid → HCID 68468693, compound

HRID 2233064Notes

Reaction equation

HRID 2233064 reaction equation
[CH3:1][O:2][C:3](=[O:35])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:16]3=[CH:17][C:18]4[C:19]([CH3:28])([CH3:27])[CH2:20][CH2:21][C:22]([CH3:26])([CH3:25])[C:23]=4[CH:24]=[C:15]3[N:14]([CH3:29])[C:13]3[CH:30]=[CH:31][C:32](Br)=[CH:33][C:12]=3[N:11]=2)=[CH:6][CH:5]=1.[CH:36]([O:38]CCCC)=[CH2:37].C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].O>[CH3:1][O:2][C:3](=[O:35])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:16]3=[CH:17][C:18]4[C:19]([CH3:28])([CH3:27])[CH2:20][CH2:21][C:22]([CH3:26])([CH3:25])[C:23]=4[CH:24]=[C:15]3[N:14]([CH3:29])[C:13]3[CH:30]=[CH:31][C:32]([C:36](=[O:38])[CH3:37])=[CH:33][C:12]=3[N:11]=2)=[CH:6][CH:5]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8108Butyl vinyl etherHCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 10768572HCID 10768572, compound

Product 1

HCID 68468693HCID 68468693, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(2-bromo-5,7,7,10,10-pentamethyl-7,8,9,10-tetrahydro-5H-5,13-diazabenzo[4,5]cyclohepta[1,2-b]naphthalen-12-yl)benzoic acid methyl ester (16, R5=CH3, Z=H, 1.9 mmol), butyl vinyl ether (4.8 mmol), Pd(OAc)2 (0.058 mmol), DPPP (0.11 mmol), K2CO3 (2.3 mmol), and H2O (0.3 mL) in DMF (5 mL) is stirred at 120° C. for 1.5 h under nitrogen atmosphere. After cooling to room temperature, the mixture is poured into 1N HCl and extracted twice with EtOAc. The combined extracts are washed with H2O, brine, dried over MgSO4 and evaporated in vacuo. The residue is purified by flash column chromatography (SiO2; hexane: EtOAc=9:1 to 3:1) to give the ester (19) (R4=CH3, Z=H, R5=CH3) as yellow solid.

Workup

  1. extractionextracted twice with EtOAc
  2. washThe combined extracts are washed with H2O, brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue is purified by flash column chromatography (SiO2; hexane: EtOAc=9:1 to 3:1)

Sources & evidence

ORD record
ord-78e797e56bb94aba8d1d1adf7dc73feb
Source dataset
uspto-grants-2010_05
Patent number
US07709470B2

Reaction notes

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