Thiomorpholine → 4-(5-Bromopyridin-2-yl)thiomorpholine

HRID 1036296Notes

Reaction equation

HRID 1036296 reaction equation
[NH:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.[Br:7][C:8]1[CH:9]=[CH:10][C:11](I)=[N:12][CH:13]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(O[Na])(C)(C)C>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([N:1]2[CH2:6][CH2:5][S:4][CH2:3][CH2:2]2)=[N:12][CH:13]=1

Participants

7

Reactant 4

HCID 67164ThiomorpholineHCID 5936905-Bromo-2-iodopyridineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 177499624-(5-Bromopyridin-2-yl)thiomorpholine

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
98 °C

Procedure

A mixture of thiomorpholine (1.03 g, 10.0 mmol), 5-bromo-2-iodopyridine (3.69 g, 13 mmol), Pd2(dba)3 (200 mg, 0.2 mmol), xantphos (510 mg, 0.6 mmol) and t-BuONa (1.44 g, 15 mmol) in toluene (50 ml) was stirred under argon at 98° C. for 3 hours. After cooled to room temperature, the mixture was filtered through celite and washed with ethyl acetate. The filtrate was evaporated and the residue was subjected to silica gel column chromatography with 0-5% ethyl acetate in hexanes as eluent to give 4-(5-bromopyridin-2-yl)thiomorpholine 219-2 as solid.

Workup

  1. temperatureAfter cooled to room temperature
  2. filtrationthe mixture was filtered through celite
  3. washwashed with ethyl acetate
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-02e3e9bd3373460cad3ec8a61014d912
Source dataset
uspto-grants-2013_10
Patent number
US08546396B2

Reaction notes

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