Sodium Carbonate → HCID 66744425, compound

HRID 1959370Notes

Reaction equation

HRID 1959370 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5](Br)=[CH:6][N:7]=1.C(OC([N:20]1[CH2:25][CH:24]=[C:23](B2OC(C)(C)C(C)(C)O2)[CH2:22][CH2:21]1)=O)(C)(C)C.C([O-])([O-])=O.[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>COCCOC.Cl[Pd]Cl.CCOC(C)=O.O>[NH2:1][C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5]([C:23]2[CH2:24][CH2:25][NH:20][CH2:21][CH:22]=2)=[CH:6][N:7]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 227251Methyl 3-Amino-6-bromopyrazine-2-carboxylateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate

Product 1

HCID 66744425HCID 66744425, compoundYield 69%

Reagents, catalysts & solvents 4

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 3-amino-6-bromo-pyrazine-2-carboxylate (6 g, 25.86 mmol), tert-butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate (7.996 g, 25.86 mmol), Na2CO3 (38.79 mL of 2 M, 77.58 mmol) and dichloropalladium; triphenylphosphane (544.5 mg, 0.7758 mmol) was stirred in DME (120.0 mL) at 100° C. for 5 hours. After this time water and EtOAc were added and the organics separated, dried and concentrated in vacuo. The residue was redissolved in DCM (20 mL) and TFA (20 mL) and the resulting solution stirred at ambient temperature for 2 hours. After this time saturated NaHCO3 was added and the organics separated, dried and concentrated. The solid was then triturated with MeOH, filtered and washed with MeOH to give the desired product as a yellow solid (4.15 g, 69%). 1H NMR (400.0 MHz, DMSO) d 2.43 (3H, s), 3.41 (2H, m), 3.80-4.02 (5H, m), 6.52 (1H, s), 7.33 (2H, s), 8.52 (1H, s) ppm; MS (ES+) 234.97

Workup

  1. customthe organics separated, dried
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was redissolved in DCM (20 mL)
  4. additionAfter this time saturated NaHCO3 was added
  5. customthe organics separated, dried
  6. concentrationconcentrated
  7. customThe solid was then triturated with MeOH
  8. filtrationfiltered
  9. washwashed with MeOH

Sources & evidence

ORD record
ord-f23a2bc19bcb4f279aa074f885c1bbce
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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