Ethyl diazoacetate → (1-Biphenyl-2-ylmethyl-2-methyl-1H-pyrrolo[3,2-c]pyridin-4-yloxy)-acetic acid ethyl ester

HRID 1445944Notes

Reaction equation

HRID 1445944 reaction equation
[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[C:12]([OH:17])[C:11]=2[CH:10]=[C:9]1[CH3:18].[N+](=[CH:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N-]>ClCCCl.ClC(Cl)C>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][O:17][C:12]1[C:11]2[CH:10]=[C:9]([CH3:18])[N:8]([CH2:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:16]=2[CH:15]=[CH:14][N:13]=1)[CH3:32]

Participants

5

Reactant 2

HCID 12192Ethyl diazoacetateHCID 178422241HCID 178422241, compound

Product 1

HCID 59170368(1-Biphenyl-2-ylmethyl-2-methyl-1H-pyrrolo[3,2-c]pyridin-4-yloxy)-acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of intermediate (5) (0.557 g, 1.77 mmole) in 1,2-dichloroethane (250 mL) rhodium(II) trifluoroacetate dimmer (0.058 g, 0.0885 mmole) was added, the reaction was heated to reflux. Then the solution of ethyl diazoacetate (90%, 0.2 mL, 1.77 mmole) in dichloroethane (35 mL) was added via a syringe pump to the mixture over 16 h. The reaction mixture was refluxed for an additional 2 h. The solvent was evaporated and the residue was purified by column chromatography (3:1 Hex:EtOAc) to afford intermediate (6) as a yellow solid. Yield: 0.272 g, 38%.

Workup

  1. temperaturethe reaction was heated to reflux
  2. temperatureThe reaction mixture was refluxed for an additional 2 h
  3. customThe solvent was evaporated
  4. customthe residue was purified by column chromatography (3:1 Hex:EtOAc)

Sources & evidence

ORD record
ord-ec5637b1cd824e6482346996e86efbb0
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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