Morpholine → HCID 46182231, compound

HRID 386475Notes

Reaction equation

HRID 386475 reaction equation
[CH2:1]([N:8]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20](Br)[CH:19]=1)[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.CC(C)([O-])C.[Na+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([N:8]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[CH:19]=1)[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23676156Sodium t-butoxideHCID 46021782HCID 46021782, compound

Product 1

HCID 46182231HCID 46182231, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of N-benzyl-N-(3-bromo-phenyl)-benzene sulfonamide (25 mg, 0.06 mmol), morpholine (6.5 μl, 0.07 mmol), palladium acetate (1 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (2 mg) and sodium tert-butoxide (21 mg, 0.22 mmol) in dioxane (1 ml) were heated to 100° C. in the microwave for 30 minutes. The reaction was filtered, diluted with water (5 ml) and extracted with dichloromethane (3×6 ml). The combined organics were filtered, concentrated in vacuo and the residues purified by preparative TLC (eluent dichloromethane) to afford the title compound as a yellow solid (18 mg, 71%) HPLC retention time 8.3 min. Mass spectrum (ES+) m/z 409 (M+H).

Workup

  1. filtrationThe reaction was filtered
  2. additiondiluted with water (5 ml)
  3. extractionextracted with dichloromethane (3×6 ml)
  4. filtrationThe combined organics were filtered
  5. concentrationconcentrated in vacuo
  6. customthe residues purified by preparative TLC (eluent dichloromethane)

Sources & evidence

ORD record
ord-3417b985d61c4acc884d441b64708e8b
Source dataset
uspto-grants-2013_02
Patent number
US08372840B2

Reaction notes

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