(Diethylamino)sulfur trifluoride → HCID 71059681, compound

HRID 1425600Notes

Reaction equation

HRID 1425600 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18]O)=[CH:12][CH:11]=1)([O-:3])=[O:2].C(N(S(F)(F)[F:26])CC)C>C(Cl)Cl>[F:26][CH2:18][CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([C:5]2[CH:6]=[N:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 71059780HCID 71059780, compound

Product 1

HCID 71059681HCID 71059681, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-(4-(4-nitropyridin-3-yl)phenyl)propan-1-ol (60 mg, 0.23 mmol) in 2 mL of dry DCM at 0° C. was added (Diethylamino)sulfur trifluoride (111 mg, 0.69 mmol) dropwise. The reaction was warmed to rt and stirred for 1 h and quenched onto ice (20 g) in saturated Na2CO3 (20 mL). The mixture was extracted with EtOAc (2×30 mL) and the organic phase was dried over MgSO4 and concentrated. The residue was purified by silica chromatography (EtOAc in hexane, 5% to 30%) to afford 3-(4-(3-fluoropropyl)phenyl)-4-nitropyridine as a pale-yellow oil (12 mg, 20%). 1H NMR (400 MHz, CDCl3): δ 8.82-8.80 (m, 2H), 7.64 (d, J=5.2, 1H), 7.33-7.27 (m, 2H), 4.55 (t, J=5.6 Hz, 1H), 4.43 (t, J=5.6 Hz, 1H), 2.82 (t, J=7.6 Hz, 2H), 2.12-1.99 (m, 2H); MS (ESI) m/z [M+H]+261.

Workup

  1. customquenched onto ice (20 g) in saturated Na2CO3 (20 mL)
  2. extractionThe mixture was extracted with EtOAc (2×30 mL)
  3. dry with materialthe organic phase was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica chromatography (EtOAc in hexane, 5% to 30%)

Sources & evidence

ORD record
ord-91e18aee0afd4fd6be97c07be33e0aa3
Source dataset
uspto-grants-2015_01
Patent number
US08932557B2

Reaction notes

Loading…