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4-Methylmorpholine → 2-Bromo-5-fluoro-4-[2-methyl-1-(2-nitro-benzenesulfonyl)-aziridin-2-yl]-pyridine

HRID 474084
Notes
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Reaction equation

HRID 474084 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]2([CH3:11])[CH2:10][NH:9]2)[C:5]([F:12])=[CH:4][N:3]=1.P(C1C=CC=CC=1)(C1C=CC=CC=1)(C1C=CC=CC=1)=O.[N+:33]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[S:42](Cl)(=[O:44])=[O:43])([O-:35])=[O:34].CN1CCOCC1>C1COCC1.O>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2([CH3:11])[CH2:10][N:9]2[S:42]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[N+:33]([O-:35])=[O:34])(=[O:43])=[O:44])[C:5]([F:12])=[CH:4][N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 13097Triphenylphosphine OxideHCID 155402-Nitrobenzenesulfonyl chlorideHCID 866680542-Bromo-5-fluoro-4-(2-methyl-aziridin-2-yl)-pyridine

Product 1

HCID 866680552-Bromo-5-fluoro-4-[2-methyl-1-(2-nitro-benzenesulfonyl)-aziridin-2-yl]-pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of crude 2-bromo-5-fluoro-4-(2-methyl-aziridin-2-yl)-pyridine (3.17 g as a 45% mixture with Ph3PO, 6.17 mmol) and 2-nitrobenzene-1-sulfonyl chloride (1.368 g, 6.17 mmol) in THF (23.15 mL) and H2O (7.72 mL) was added N-methylmorpholine and the reaction mixture was stirred at rt for 1.5 h. Alox neutral (2-3 spatula) was added and the reaction mixture was filtered through celite, washed with DCM and the filtrates were diluted with DCM and 1M aq. NaHCO3 soln. The phases were separated and the aq. phase was reextracted twice with DCM. The combined org. phases were dried over Na2SO4 and concentrated. Flash chromatography on silica gel (heptane:EtOAc 4:1 to 3:1) followed by recrystallization from EtOAc/hexane yielded the title compound as a colourless solid. HPLC RtH4=1.11 min; ESIMS: 416, 418 [(M+H)+]; 1H NMR (400 MHz, CDCl3): δ 8.31-8.30 (m, 1H), 8.23 (d, 1H), 7.86-7.77 (m, 3H), 7.68 (d, 1H), 3.28 (s, 1H), 2.78 (s, 1H), 2.09 (s, 3H).

Workup

  1. additionAlox neutral (2-3 spatula) was added
  2. filtrationthe reaction mixture was filtered through celite
  3. washwashed with DCM
  4. additionthe filtrates were diluted with DCM and 1M aq. NaHCO3 soln
  5. customThe phases were separated
  6. dry with materialphases were dried over Na2SO4
  7. concentrationconcentrated
  8. customFlash chromatography on silica gel (heptane:EtOAc 4:1 to 3:1) followed by recrystallization from EtOAc/hexane

Sources & evidence

ORD record
ord-f6bb891f7ae14b9dbc5b576d555e5da3
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08637508B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes