1,2-Dimethoxyethane → Methyl 2-[3-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-4-pyridinyl]benzoate

HRID 1007084Notes

Reaction equation

HRID 1007084 reaction equation
COCCOC.Br[C:8]1[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11].[C:18]([O:22][C:23]([NH:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][C:32]=1B(O)O)=[O:24])([CH3:21])([CH3:20])[CH3:19].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:18]([O:22][C:23]([NH:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][C:32]=1[C:8]1[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11])=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 11894Methyl 2-bromobenzoateHCID 10999519(3-{[(tert-Butoxycarbonyl)amino]methyl}pyridin-4-yl)boronic acid

Product 1

HCID 11046130Methyl 2-[3-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-4-pyridinyl]benzoateYield 84%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

20 ml of 1,2-dimethoxyethane were aerated with argon, and 230 mg (0.2 mmol) of Pd(PPh3)4 and 0.86 g (4 mmol) of methyl 2-bromobenzoate were added. After 10 min, 1.51 g (6 mmol) of 3-(tert-butoxycarbonylaminomethyl)pyridine-4-boronic acid and finally 4 ml of a 2M sodium carbonate solution were added. The mixture was heated to reflux under argon for 13 h, diluted with dichloromethane after cooling and washed with water. The organic phase was dried, concentrated and purified by chromatography on silica gel. 1.15 g (84%) of a viscous pale yellow oil were obtained. MS (ES+): m/z=343 (M+1).

Workup

  1. additionwere added
  2. temperatureThe mixture was heated
  3. temperatureto reflux under argon for 13 h
  4. temperatureafter cooling
  5. washwashed with water
  6. customThe organic phase was dried
  7. concentrationconcentrated
  8. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-37d854d9b928488c9a0e76ac762d5d53
Source dataset
uspto-grants-2004_09
Patent number
US06794377B2

Reaction notes

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