Morpholine → HCID 82582561, compound

HRID 926264Notes

Reaction equation

HRID 926264 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[CH:7]1[C:8]2[C:3](=[C:2]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][N:6]=1

Participants

8

Reactant 3

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 7364875-Bromoisoquinoline

Product 1

HCID 82582561HCID 82582561, compoundYield 99.3%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-bromoisoquinoline (4.07 g, 19.6 mmol), morpholine (3.41 mL, 39.1 mmol), Cs2CO3 (12.75 g, 39.1 mmol), Pd(OAc)2 (220 mg, 0.98 mmol) and BINAP (609 mg, 0.98 mmol) in toluene (160 mL) was heated at 110° C. for 6 h under N2. The mixture was then concentrated in vacuo and the black residue obtained was taken up in DCM and filtered over Celite. The filtrate was concentrated in vacuo and the brown oil obtained was purified by flash chromatography (SiO2, cHex to AcOEt) to give the title compound (4.17 g) as a brown oil. UPLC-MS: MS 215.1 (M+H+); UPLC rt 0.57 min.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customthe black residue obtained
  3. filtrationfiltered over Celite
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe brown oil obtained
  6. customwas purified by flash chromatography (SiO2, cHex to AcOEt)

Sources & evidence

ORD record
ord-a519ae2319444d3b88fabaa9e3d2ad2e
Source dataset
uspto-grants-2016_03
Patent number
US09284331B2

Reaction notes

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