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1,2-Dimethoxyethane → Ethyl 6-[2-(tert-butoxycarbonylaminomethyl)phenyl]pyridine-2-carboxylate

HRID 395356
Notes
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Reaction equation

HRID 395356 reaction equation
COCCOC.Br[C:8]1[N:13]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]=[CH:10][CH:9]=1.[C:19]([O:23][C:24]([NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1B(O)O)=[O:25])([CH3:22])([CH3:21])[CH3:20].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:19]([O:23][C:24]([NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:8]1[N:13]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]=[CH:10][CH:9]=1)=[O:25])([CH3:22])([CH3:20])[CH3:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2758810Ethyl 6-BromopicolinateHCID 10911965(2-(((tert-Butoxycarbonyl)amino)methyl)phenyl)boronic acid

Product 1

HCID 22345551Ethyl 6-[2-(tert-butoxycarbonylaminomethyl)phenyl]pyridine-2-carboxylateYield 72%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

83 ml of 1,2-dimethoxyethane were aerated with argon, and 481 mg (0.41 mmol) of Pd(PPh3)4 and 1.9 g (8.3 mmol) of ethyl 6-bromopicolinate were added. After 10 min, 3.16 g (12.5 mmol) of 2-(tert-butoxycarbonylaminomethyl)phenylboronic acid and finally 8.3 ml of a 2M sodium carbonate solution were added. The mixture was heated to reflux under argon for 18 h, diluted with dichloromethane after cooling and washed with water. The organic phase was dried, concentrated and purified by chromatography on silica gel. 2.12 g (72%) of a viscous orange oil were obtained.

Workup

  1. additionwere added
  2. temperatureThe mixture was heated
  3. temperatureto reflux under argon for 18 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-4891c758d3744acea9f210cf9f6c0ba0
Source dataset
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06605625B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes