Morpholine → HCID 68550595, compound

HRID 1868116Notes

Reaction equation

HRID 1868116 reaction equation
Cl[C:2]1[CH:30]=[CH:29][C:5]2[S:6][C:7]([S:10]([N:13]3[CH2:18][CH2:17][N:16]([C:19]4[C:24]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:22]=[CH:21][N:20]=4)[CH2:15][CH2:14]3)(=[O:12])=[O:11])=[C:8]([CH3:9])[C:4]=2[CH:3]=1.C(O[Na])(C)(C)C.[NH:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:9][C:8]1[C:4]2[CH:3]=[C:2]([N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)[CH:30]=[CH:29][C:5]=2[S:6][C:7]=1[S:10]([N:13]1[CH2:18][CH2:17][N:16]([C:19]2[C:24]([C:25]([F:26])([F:28])[F:27])=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:15][CH2:14]1)(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 68549409HCID 68549409, compoundHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 68550595HCID 68550595, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

1-(5-chloro-3-methyl-benzo[b]thiophene-2-sulfonyl)-4-(3-trifluoromethyl-pyridin-2-yl)-piperazine (142.5 mg, 0.3 mmol), Pd2(dba)3 (13.7 mg, 0.015 mmol), t-BuONa (82.7 mg, 0.84 mmol) and the ligand (9 mg, 0.03 mmol) were mixed in a sealed tube which was flushed with N2. To this was added tolene (2 mL) and then morpholine (21 μL, 0.24 mmol). The resultant mixture was heated at 80° C. for 4 hours. The solvent was removed under vacuum and the crude product was purified with flash column chromatography to yield 4-{3-Methyl-2-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazine-1-sulfonyl]-benzo[b]thiophen-5-yl}-morpholine in 52% yield (82 mg) as white solid. HRMS: calcd for C23H25F3N4O3S2+H+, 527.13929. found (ESI-FTMS, [M+H]1+), 527.1392.

Workup

  1. customwas flushed with N2
  2. additionTo this was added tolene (2 mL)
  3. customThe solvent was removed under vacuum
  4. customthe crude product was purified with flash column chromatography

Sources & evidence

ORD record
ord-e7324caf47954f5f885c367b5b1af16a
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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