Potassium Carbonate → Methyl 3-amino-6-bromo-6'-morpholino-2,3'-bipyridine-4-carboxylate

HRID 2410751Notes

Reaction equation

HRID 2410751 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[N:13][CH:14]=2)O1.[NH2:22][C:23]1[C:32](Br)=[N:31][C:30]([Br:34])=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26].C([O-])([O-])=O.[K+].[K+]>>[NH2:22][C:23]1[C:32]([C:9]2[CH:14]=[N:13][C:12]([N:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)=[CH:11][CH:10]=2)=[N:31][C:30]([Br:34])=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 27953634-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl)morpholineHCID 53419616Methyl 3-amino-2,6-dibromoisonicotinate

Product 1

HCID 86663022Methyl 3-amino-6-bromo-6'-morpholino-2,3'-bipyridine-4-carboxylateYield 42.8%

Conditions

Temperature
100 °C

Procedure

A mixture of 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine (400 mg, 1.379 mmol), methyl 3-amino-2,6-dibromoisonicotinate (427 mg, 1.379 mmol), tetra(triphenylphospine)palladium(0) (159 mg, 0.138 mmol), K2CO3 (762 mg, 5.51 mmol) in a microwave vial was flushed with nitrogen and DMF (4.0 mL) was added. The vial was sealed heated at 100° C. overnight. The reaction was diluted with EtOAc and water to give a precipitate. This was collected by filtration, washed with water and EtOAc to leave methyl 3-amino-6-bromo-6′-morpholino-2,3′-bipyridine-4-carboxylate (232 mg, 0.590 mmol, 42.8% yield) as a light green solid. 1H NMR (400 MHz, chloroform-d) δ ppm 8.49 (1H, d, J=1.76 Hz), 7.70-7.82 (2H, m), 6.71 (1H, d, J=8.81 Hz), 5.93 (2H, br. s.), 3.91 (3H, s), 3.76-3.86 (4H, m), 3.46-3.63 (4H, m).

Workup

  1. customwas flushed with nitrogen and DMF (4.0 mL)
  2. additionwas added
  3. customThe vial was sealed
  4. additionThe reaction was diluted with EtOAc and water
  5. customto give a precipitate
  6. filtrationThis was collected by filtration
  7. washwashed with water and EtOAc

Sources & evidence

ORD record
ord-aa46ce5be8a24f129c8a0cf5bec12a1f
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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