Tetrahydrofuran → HCID 117987912, compound

HRID 63792Notes

Reaction equation

HRID 63792 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[C:11]3=[CH:20][C:21]([C:23]([N:25]([CH3:27])[CH3:26])=O)=[CH:22][N:10]3[N:9]=2)=[CH:4][CH:3]=1.O1CCCC1.CSC.B>O1CCOCC1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[C:11]3=[CH:20][C:21]([CH2:23][N:25]([CH3:27])[CH3:26])=[CH:22][N:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 12423031(Dimethyl sulfide)trihydroboronHCID 117988523HCID 117988523, compound

Product 1

HCID 117987912HCID 117987912, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1 g of compound 12a (2.7 mmol) and 50 mL of tetrahydrofuran or dioxane were added into a 150 mL two-neck flask and refluxed under nitrogen atmosphere. 2 M of borane-dimethyl sulfide solution (10.8 mmol) was slowly added dropwise and refluxed for 2 hours. The reaction mixture was quenched with methanol and purified by column chromatography with dichloromethane to give white solid 13a (930 mg, 96.7%). m.p. 205° C. (decomposition). 1H NMR (300 MHz, DMSO-d6): δ 7.92 (d, J=8.5 Hz, 2H), 7.86 (s, 1H), 7.05 (s, 1H), 6.60 (d, J=8.5 Hz, 2H), 5.48 (br s, 2H), 4.02 (t, J=4.5 Hz, 4H), 3.92 (s, 2H), 3.77 (t, J=4.5 Hz, 4H), 2.42 (s, 6H). MS (EI) m/e (%): 352 (M+, 24).

Workup

  1. temperaturerefluxed under nitrogen atmosphere
  2. temperaturerefluxed for 2 hours
  3. customThe reaction mixture was quenched with methanol
  4. custompurified by column chromatography with dichloromethane

Sources & evidence

ORD record
ord-8e253285c0b84cc5bc554c05ae077160
Source dataset
uspto-grants-2016_09
Patent number
US09447101B2

Reaction notes

Loading…