Dichloromethane → HCID 15594672, compound

HRID 1524166Notes

Reaction equation

HRID 1524166 reaction equation
Br[C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl>C(OCC)(=O)C.O.O1CCOCC1>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 6428002-BromopyrazineHCID 27343222-Chlorophenylboronic acid

Product 1

HCID 15594672HCID 15594672, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Bromopyrazine (100 mg, 0.630 mmol) and ((2-chlorophenyl)boronic acid (103 mg, 0.660 mmol) were added to a 5 mL sealable vial equipped with a stir-bar. A solution consisting of 1,4-dioxane (3 mL) and Na2CO3 (1.6 mL, 2 M) was added and the mixture sparged with argon for 10 minutes before adding Pd(ddp)Cl2.CH2Cl2 (23 mg, 0.031 mmol) and heating at 80° Celsius for 15 hours. The reaction was then cooled to rt, diluted with 5 mL of ethyl acetate and 5 mL of water, and the mixture extracted with ethyl acetate (3×20 mL). The combined organic extracts were then dried with sodium sulfate and concentrated to dryness. The resultant residue was subjected to FCC to provide the title compound. 1H NMR (500 MHz, CDCl3) δ 8.98-8.96 (d, J=1.6, 1H), 8.70-8.68 (dd, J=2.5, 1.6, 1H), 8.58-8.56 (d, J=2.6, 1H), 7.66-7.58 (m, 1H), 7.54-7.50 (m, 1H), 7.43-7.39 (m, 2H).

Workup

  1. customequipped with a stir-bar
  2. additionwas added
  3. customthe mixture sparged with argon for 10 minutes
  4. additionbefore adding Pd(ddp)Cl2
  5. extractionthe mixture extracted with ethyl acetate (3×20 mL)
  6. dry with materialThe combined organic extracts were then dried with sodium sulfate
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-01a47b47220e4cac9a6561b4e1a4ab00
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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