Dichloromethane → HCID 90313071, compound

HRID 1523908Notes

Reaction equation

HRID 1523908 reaction equation
Br[C:2]1[N:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[Br:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[C:14]([F:21])[CH:13]=1.C(Cl)Cl.C([O-])([O-])=O.[K+].[K+]>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.O1CCOCC1>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[N:3]=[C:4]3[CH:5]=[CH:6][NH:7][C:8]3=[N:9][CH:10]=2)=[C:14]([F:21])[CH:13]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 27733334-Bromo-2-fluorobenzeneboronic acidHCID 250673082-bromo-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 90313071HCID 90313071, compoundYield 35%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

To a 150 mL screw-cap vessel under nitrogen was added 5-bromo-4,7-diazaindole (1.0 g, 5.05 mmol), 4-bromo-2-fluorophenyl boronic acid (1.33 g, 6.06 mmol), Pd(dppf)Cl2.CH2Cl2 (0.2 g, 0.24 mmol), K2CO3 (2.09 g, 15.2 mmol), 1,4-dioxane (35 mL) and water (13 mL). The mixture was sparged with nitrogen for 10 minutes, the vessel capped and the reaction heated at 95° Celsius for 24 hours. The reaction was then cooled to rt, diluted with ethyl acetate (200 mL) and washed with water (1×100 mL) and brine (1×100 mL). The organic layer was dried with Na2SO4 and evaporated to dryness. The crude product was purified by HPLC giving the title compound (515 mg, 35%). MS (ESI): mass calcd. for C12H7BrFN2, 290.98; m/z found, 292.0 [M+H]+.

Workup

  1. customTo a 150 mL screw-cap vessel under nitrogen
  2. customThe mixture was sparged with nitrogen for 10 minutes
  3. customthe vessel capped
  4. temperatureThe reaction was then cooled to rt
  5. additiondiluted with ethyl acetate (200 mL)
  6. washwashed with water (1×100 mL) and brine (1×100 mL)
  7. dry with materialThe organic layer was dried with Na2SO4
  8. customevaporated to dryness
  9. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-2657e9eb91db4962b6f6a58b16ced0cf
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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