Sodium Carbonate → HCID 40480512, compound

HRID 1260473Notes

Reaction equation

HRID 1260473 reaction equation
Br[C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[Cl:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1>COCCOC.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:15][C:16]1[CH:21]=[C:20]([C:2]2[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 6428163-Amino-2-bromopyridineHCID 2734323(3-Chlorophenyl)boronic acid

Product 1

HCID 40480512HCID 40480512, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 2-bromopyridin-3-amine in DME (0.1M) were added 2M aqueous Na2CO3 solution (2 eq.) and (3-chlorophenyl)boronic acid (1.1 eq). The mixture was degassed and placed under an argon atmosphere. PdCl2(dppf) (0.02 eq) were added and the reaction was heated at reflux overnight under argon. After cooling the reaction was diluted with EtOAc and washed with water and brine, then dried and evaporated under reduced pressure to afford the titled compound which was used as such in the next step. MS (ES+) C11H9ClN2 requires 204, 206, found: 205, 207 (M+H)+.

Workup

  1. customThe mixture was degassed
  2. temperaturethe reaction was heated
  3. temperatureat reflux overnight under argon
  4. temperatureAfter cooling the reaction
  5. washwashed with water and brine
  6. customdried
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0b69e2b684e5436d971ac1d6822a2cb1
Source dataset
uspto-grants-2013_06
Patent number
US08470823B2

Reaction notes

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