Morpholine → HCID 21084072, compound

HRID 347906Notes

Reaction equation

HRID 347906 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[CH:11][C:10]3[C:15]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[S:17][C:9]2=3)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[O:38]1[CH2:39][CH2:40][N:35]([C:2]2[CH:7]=[CH:6][C:5]([N:8]3[C:13](=[O:14])[CH:12]=[CH:11][C:10]4[C:15]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[S:17][C:9]3=4)=[CH:4][CH:3]=2)[CH2:36][CH2:37]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 21084063HCID 21084063, compound

Product 1

HCID 21084072HCID 21084072, compoundYield 39.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of the compound of Example 57 (100 mg, 0.22 mmol), caesium carbonate (101 mg, 0.31 mmol), Pd(OAc)2 (5 mg, 0.022 mmol, 10 mol %) and 2,2′-bis(diphenylphosphino)-1-1′-binaphthyl (BINAP) (21 mg, 0.033 mmol, 15 mol %) in toluene (2 mL) and under nitrogen was added morpholine (0.024 mL, 0.27 mmol). The reaction mixture was heated to 100° for 18 h. Solvent was removed in vacuo and the crude product purified by chromatography on silica (0–20% THF in DCM) to give the title compound as a white solid (40 mg).

Workup

  1. temperatureThe reaction mixture was heated to 100° for 18 h
  2. customSolvent was removed in vacuo
  3. customthe crude product purified by chromatography on silica (0–20% THF in DCM)

Sources & evidence

ORD record
ord-e611cc8b1cb645e5aa1be83a3c482af2
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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