Triethylamine → HCID 18796899, compound

HRID 1003407Notes

Reaction equation

HRID 1003407 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8](Cl)[N:9]=2)[S:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13].[S:16]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17]1.C(N(CC)CC)C>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]>[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:18]3[CH:19]=[CH:20][S:16][CH:17]=3)[N:9]=2)[S:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 581760Thiophene-3-boronic acidHCID 18796944HCID 18796944, compound

Product 1

HCID 18796899HCID 18796899, compoundYield 88%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
95 °C

Procedure

A solution of the methyl 7-amino-2-chlorothieno[2,3-bjpyrazine-6carboxylate prepared as described in Example 10C (0.190 g), thiophene-3-boronic acid (0.100 g), Pd(dppf)Cl2 (0.032 g) and triethylamine (0.22 mL) in degassed DMF was heated to 95° C. for 4 h, cooled, quenched in water and extracted with 1:1Et2O/EtOAc (3×). The organics were washed 3× with water, brine, dried (Na2SO4), filtered and solvent evaporated to give 0.200 g (88%) of the title compound: 1H NMR (300 MHz, CDCl3) δ 3.95 (3H, s), 6.23 (2H, br s), 7.50 (1H, dd), 7.79 (1H, dd), 8.05 (1H, dd), 9.00 (1H, s).

Workup

  1. temperaturecooled
  2. customquenched in water
  3. extractionextracted with 1:1Et2O/EtOAc (3×)
  4. washThe organics were washed 3× with water, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customsolvent evaporated

Sources & evidence

ORD record
ord-75d7e5c2639f4b649c93cf73d3bf9d95
Source dataset
uspto-grants-2000_04
Patent number
US06046207

Reaction notes

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