Sodium Carbonate → HCID 86663058, compound

HRID 2410835Notes

Reaction equation

HRID 2410835 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10](B(O)O)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].[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]>>[NH2:22][C:23]1[C:32]([C:10]2[CH:11]=[CH:12][C:7]([N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)=[CH:8][CH:9]=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 10340Sodium CarbonateHCID 2795359(4-(Morpholin-4-yl)phenyl)boronic acidHCID 53419616Methyl 3-amino-2,6-dibromoisonicotinate

Product 1

HCID 86663058HCID 86663058, compoundYield 466.5%

Conditions

Temperature
110 °C

Procedure

A mixture of 4-morpholinophenylboronic acid (5.0 g, 24 mmol), sodium carbonate (6.91 g, 65.2 mmol), tetrakistriphenylphosphine palladium (0) (1.40 g, 1.21 mmol), and methyl 3-amino-2,6-dibromoisonicotinate (7.86 g, 25 4 mmol) in a pressure flask was flushed with nitrogen. Toluene (60 mL) and methanol (20 mL) were added and the flask was sealed heated at 110° C. for 44 h. After cooling to RT, the solid was collected by filtration and washed with sat. aq. NaHCO3 solution, water, and dried to give methyl 3-amino-6-bromo-2-(4-morpholinophenyl)-isonicotinate (7.32 gm, 77%). MS (ESI) m/z 392.15 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 7.78 (1H, s), 7.58 (2H, d, J=8.85 Hz), 7.01 (2H, d, J=8.85 Hz), 6.00 (2H, br. s.), 3.94 (3H, s), 3.88-3.92 (4H, m), 3.22-3.28 (4H, m).

Workup

  1. customwas flushed with nitrogen
  2. additionToluene (60 mL) and methanol (20 mL) were added
  3. customthe flask was sealed
  4. temperatureAfter cooling to RT
  5. filtrationthe solid was collected by filtration
  6. washwashed with sat. aq. NaHCO3 solution, water
  7. customdried

Sources & evidence

ORD record
ord-46dad70a16c74729a1418136f26c2b8c
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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