Sodium Carbonate → HCID 10135370, compound

HRID 2179995Notes

Reaction equation

HRID 2179995 reaction equation
Cl[C:2]1[C:7]([CH2:8][CH3:9])=[N:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[O:18][CH3:19])=[C:4]([CH2:20][CH3:21])[N:3]=1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCOC(C)=O.CCCCCC.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>[CH3:19][O:18][C:11]1[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:10]=1[C:5]1[C:4]([CH2:20][CH3:21])=[N:3][C:2]([C:29]2[CH:28]=[C:27]([F:30])[CH:26]=[CH:25][C:24]=2[O:23][CH3:22])=[C:7]([CH2:8][CH3:9])[N:6]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27826735-Fluoro-2-methoxyphenylboronic acidHCID 22248864HCID 22248864, compound

Product 1

HCID 10135370HCID 10135370, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 8058HexaneSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Pd(PPh3)4 (8 mg) is added to a solution of 2-chloro-5-(2,4-dimethoxy-phenyl)-3,6-diethyl-pyrazine (70 mg) in DME (2 ml) at room temperature, followed by 2-methoxy-5-fluorophenylboronic acid (45 mg) and Na2CO3 (1M, 0.5 ml). The resulting mixture is heated to 90° C. for 20 hours, then cooled to room temperature. The reaction mixture is diluted with 50% EtOAc in hexane and washed with water and brine, dried, filtered and evaporated. The crude is purified by chromatography (eluted with 15% EtOAc in hexane) to give 2-(2,4-Dimethoxy-phenyl)-3,6-diethyl-5-(5-fluoro-2-methoxy-phenyl)-pyrazine compound 3. MS: 397.3 (M+1).

Workup

  1. temperaturecooled to room temperature
  2. washwashed with water and brine
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude is purified by chromatography (eluted with 15% EtOAc in hexane)

Sources & evidence

ORD record
ord-e477b4b2af3b4fa296edda1fa9f98ccb
Source dataset
uspto-grants-2005_05
Patent number
US06887875B2

Reaction notes

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