Sodium Carbonate → HCID 59765138, compound

HRID 536206Notes

Reaction equation

HRID 536206 reaction equation
[Cl:1][C:2]1[C:7](I)=[C:6]([NH2:9])[CH:5]=[CH:4][N:3]=1.[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([C:26]#[C:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[CH:23]=[CH:24][CH:25]=1>CN(C=O)C.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].O>[Cl:1][C:2]1[C:7]2[C:26]([C:22]3[CH:23]=[CH:24][CH:25]=[C:20]([O:19][CH3:18])[CH:21]=3)=[C:27]([Si:28]([CH3:31])([CH3:29])[CH3:30])[NH:9][C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 4407093(3-Methoxyphenylethynyl)trimethylsilaneHCID 242292082-Chloro-3-iodopyridin-4-amine

Product 1

HCID 59765138HCID 59765138, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

7.6 g (30 mmol) of 2-chloro-3-iodopyridin-4-ylamine from Example B1, 1.7 g (41 mmol) of lithium chloride and 15.9 g (120 mmol) of sodium carbonate are dissolved in 100 ml of DMF, and 8 g (39 mmol) of commercial (3-methoxyphenyl)ethynyltrimethylsilane and 4.9 g (6 mmol) of commercial Pd(dppf)2Cl2*H2Cl2 are added at 100° C. under nitrogen. The mixture is stirred at the temperature indicated for 12 h and subsequently poured at room temperature (RT) into water and extracted with ethyl acetate. The organic phase is concentrated and purified by chromatography over silica gel. The combined product fractions (5.3 g; 53%; pale-brown oil) are used for the subsequent reaction.

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic phase is concentrated
  3. custompurified by chromatography over silica gel
  4. customThe combined product fractions (5.3 g; 53%; pale-brown oil) are used for the subsequent reaction

Sources & evidence

ORD record
ord-7d482365f65d4cef9d1d7cbe1af86923
Source dataset
uspto-grants-2014_10
Patent number
US08859581B2

Reaction notes

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