(Bis(2-methoxyethyl)amino)sulfur trifluoride → HCID 86303960, compound

HRID 2271476Notes

Reaction equation

HRID 2271476 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH:16]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)O)[CH:11]=[N:12][C:13]=2[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1.COCCN(S(F)(F)[F:35])CCOC>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH3:15])=[N:12][CH:11]=[C:10]([CH:16]([F:35])[C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 86303956HCID 86303956, compound

Product 1

HCID 86303960HCID 86303960, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [5-(3-chlorophenyl)-6-methoxypyridin-3-yl](4-fluorophenyl)methanol (Example 14, 70 mg, 0.18 mmol) in DCM (1 mL) was added Deoxo-Fluor® (79 mg, 0.36 mmol). The solution was stirred at room temperature for 1 h then concentrated under reduced pressure. Purification (FCC, SiO2, 0-10% EtOAc/hexanes) afforded the title compound (21 mg, 34%). 1H NMR (400 MHz, CD3OD) δ 8.13 (s, 1H), 7.62 (d, J=2.0 Hz, 1H), 7.52 (s, 1H), 7.47-7.31 (m, 5H), 7.15 (t, J=8.8 Hz, 2H), 6.70-6.52 (m, 1H), 3.96 (s, 3H). [M+H]=346.17.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customPurification (FCC, SiO2, 0-10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c8d2210c9dfd4613bdaad3f53f001acf
Source dataset
uspto-grants-2015_09
Patent number
US09120770B2

Reaction notes

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