Sodium Carbonate → N-(3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)phenyl)acrylamide

HRID 1500825Notes

Reaction equation

HRID 1500825 reaction equation
C([NH:5]C1C=C(B(O)O)C=CC=1)(=O)C=C.C([O-])([O-])=O.[Na+].[Na+].[CH3:21][C:22]1[C:30]2[C:25](=[N:26][CH:27]=[C:28]([C:31]3[CH:32]=[C:33]([NH:37][C:38](=[O:41])[CH:39]=[CH2:40])[CH:34]=[CH:35][CH:36]=3)C=2)[NH:24]N=1>C1(C)C=CC=CC=1.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]>[N:5]1[C:28]([C:31]2[CH:32]=[C:33]([NH:37][C:38](=[O:41])[CH:39]=[CH2:40])[CH:34]=[CH:35][CH:36]=2)=[CH:27][N:26]=[C:25]2[NH:24][CH:21]=[CH:22][C:30]=12

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 103213313-Acrylamidophenylboronic acidHCID 178460022HCID 178460022, compound

Product 1

HCID 86300986N-(3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)phenyl)acrylamide

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 21 (100 mg, 0.507 mmol) and 2 (84 mg, 0.507 mmol) in toluene and ethanol (4:1 mL) was added Na2CO3 (111.01 mg, 1.014 mmol). The reaction was degassed and purged with nitrogen for 10 min. Pd(dppf)Cl2 (20.7 mg, 0.025 mmol) was added to the reaction. The reaction was degassed and purged with nitrogen for another 10 min. The reaction was heated to 90° C. under sealed condition overnight, allowed to cool to RT, and diluted with chloroform. The organic layer was filtered through Celite and concentrated to get the crude, which was purified through flash chromatography by using 100-200 mesh silica gel. The compound was eluted in 40% ethyl acetate in hexane as an off-white solid 22. MS-ES+264.8; 1H NMR (400 MHz, DMSO-D6) 22: 9.99 (bs, 1H), 9.40 (bs, 1H), 7.25 (bs, 1H), 7.08 (m, 1H), 7.00 (d, 1H), 6.42 (m, 2H), 6.21 (m, 1H), 5.71 (m, 1H).

Workup

  1. customThe reaction was degassed
  2. custompurged with nitrogen for 10 min
  3. customThe reaction was degassed
  4. custompurged with nitrogen for another 10 min
  5. customunder sealed condition overnight
  6. temperatureto cool to RT
  7. additiondiluted with chloroform
  8. filtrationThe organic layer was filtered through Celite
  9. concentrationconcentrated
  10. customto get the crude, which
  11. customwas purified through flash chromatography
  12. washThe compound was eluted in 40% ethyl acetate in hexane as an off-white solid 22

Sources & evidence

ORD record
ord-5d1289de9dd344bf8b0d1ebea005a164
Source dataset
uspto-grants-2015_12
Patent number
US09206188B2

Reaction notes

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