1,2-Dimethoxyethane → Methyl 3-[2-(tert-butoxycarbonylaminomethyl)phenyl]pyrazine-2-carboxylate

HRID 1007082Notes

Reaction equation

HRID 1007082 reaction equation
COCCOC.Br[C:8]1[C:9]([C:14]([O:16][CH3:17])=[O:15])=[N:10][CH:11]=[CH:12][N:13]=1.[C:18]([O:22][C:23]([NH:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=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:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:8]1[C:9]([C:14]([O:16][CH3:17])=[O:15])=[N:10][CH:11]=[CH:12][N:13]=1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 10911965(2-(((tert-Butoxycarbonyl)amino)methyl)phenyl)boronic acidHCID 13318551Methyl 3-bromopyrazine-2-carboxylate

Product 1

HCID 12017231Methyl 3-[2-(tert-butoxycarbonylaminomethyl)phenyl]pyrazine-2-carboxylateYield 19%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

107 ml of 1,2-dimethoxyethane were aerated with argon, and 597 mg (0.51 mmol) of Pd(PPh3)4 and 2.24 g (10.3 mmol) of methyl 3-brompyrazine-2-carboxylate were added. After 10 min, 3.9 g (15.45 mmol) of 2-(tert-butoxycarbonylaminomethyl)-phenylboronic acid and finally 10.7 ml of a 2M sodium carbonate solution were added. The mixture was heated to reflux for 18 h under argon, diluted with dichloromethane after cooling and washed with water. The organic phase was dried, concentrated and purified by chromatography on silica gel. 661 mg (19%) of a viscous oil were obtained. MS (ES+): m/z=344 (M+1), 288 (M−55). 1H-NMR (CDCl3): δ=8.78 (1H, d, J=2.4 Hz), 8.67 (1H, d, J=2.4 Hz), 7.54-7.14 (4H, m), 5.11 (1H, br s), 4.22 (2H, d, J=5.9 Hz), 3.79 (3H, s), 1.38 (9H, s).

Workup

  1. additionwere added
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 18 h under argon
  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-8629ea31ea004f7dac1b24d311a4849a
Source dataset
uspto-grants-2004_09
Patent number
US06794377B2

Reaction notes

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