Morpholine → HCID 46913522, compound

HRID 1025390Notes

Reaction equation

HRID 1025390 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:12]=[N:13][C:14]([O:19][CH3:20])=[C:15]([O:17][CH3:18])[CH:16]=3)=[CH:9][N:10]=2)[CH:7]=1.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:18][O:17][C:15]1[CH:16]=[C:11]([C:8]2[N:6]3[CH:7]=[C:2]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[CH:3]=[CH:4][C:5]3=[N:10][CH:9]=2)[CH:12]=[N:13][C:14]=1[O:19][CH3:20]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 46913420HCID 46913420, compound

Product 1

HCID 46913522HCID 46913522, compoundYield 19.6%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a 5 mL microwave tube was added 6-bromo-3-(5,6-dimethoxypyridin-3-yl)imidazo[1,2-a]pyridine (0.050 g, 0.15 mmol), morpholine (0.020 g, 0.22 mmol), 2-(diphenylphosphino)-1-(2-(diphenylphosphino)naphthalen-1-yl)naphthalene (0.0028 g, 0.0045 mmol), Tris(dibenzylideneacetone)dipalladium(0) (0.0014 g, 0.0015 mmol), sodium tert-butoxide (0.020 g, 0.21 mmol), and toluene (3 mL). The resulting reaction mixture was sealed and heated to 100° C. in closed system for 6 h. The reaction was cooled and the solvent was removed. The crude product was purified using SiO2 chromatography (Teledyne Isco RediSep®, 12 g SiO2, DCM:MeOH=96%:4%, Flow=30 mL/min). The product fractions were collected. The solvent was removed in vacuo to afford the desired product as white solid (10.0 mg). MS (ESI pos. ion) m/z: 341.0. Calcd exact mass for C18H20N4O3: 340.2. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 2.99-3.09 (m, 4H) 3.84-3.92 (m, 4H) 3.94 (s, 3H) 4.11 (s, 3H) 7.12 (d, J=9.79 Hz, 1H) 7.17 (s, 1H) 7.57-7.65 (m, 3H) 7.96 (s, 1H).

Workup

  1. customThe resulting reaction mixture
  2. customwas sealed
  3. temperatureThe reaction was cooled
  4. customthe solvent was removed
  5. customThe crude product was purified
  6. customThe product fractions were collected
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6ef55eaa4be540a4938921fb730a84e2
Source dataset
uspto-grants-2014_05
Patent number
US08729074B2

Reaction notes

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