Sodium Bicarbonate → Fluoro-quinolin-6-yl-acetonitrile

HRID 655227Notes

Reaction equation

HRID 655227 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][C:12]#[N:13])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C([Li])(C)(C)C.[F:19]N(S(C1C=CC=CC=1)(=O)=O)S(C1C=CC=CC=1)(=O)=O.C([O-])(O)=O.[Na+]>O1CCCC1.O>[F:19][CH:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][CH:3]=[CH:4]2)[C:12]#[N:13]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 588007N-FluorobenzenesulfonimideHCID 21992552(Quinolin-6-yl)acetonitrileHCID 178418306HCID 178418306, compound

Product 1

HCID 68704293Fluoro-quinolin-6-yl-acetonitrileYield 44.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of quinolin-6-yl-acetonitrile (1.06 g, 6.3 mmol) in tetrahydrofuran (40 mL) was cooled to −78° C. to which tert-butyl lithium (0.8 M in pentane, 7.6 mmol, 7.9 mL) was added in a dropwise fashion over 10 minutes. After the addition was complete the mixture was stirred at −78° C. for 30 min before a solution of N-fluorodi(benzenesulfonyl)-amine (1.5 eq., 9.45 mmol, 3.0 g) in tetrahydrofuran (10 mL) was added. The reaction mixture was stirred for 2 hours at −78° C. before water was added followed by aqueous NaHCO3. The mixture was extracted with dichloromethane (3×80 mL), dried (Na2SO4) and concentrated in vacuo onto silica gel and purified via flash column chromatography (SiO2, hexane:ethyl acetate 100/0-50/50) to return the title compound as a red solid (520 mg, 2.8 mmol, 44%). 1H NMR 500 MHz (DMSO-d6) δ 6.05 (1H, d), 7.66 (1H, dd), 7.95 (1H, dd), 8.19 (1H, d), 8.32 (1H, t), 8.55 (1H, d), 9.03 (1H, dd); MS (m/z) 187 [M+H+]+.

Workup

  1. additionwas added in a dropwise fashion over 10 minutes
  2. additionAfter the addition
  3. additionwas added
  4. additionwas added
  5. extractionThe mixture was extracted with dichloromethane (3×80 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo onto silica gel
  8. custompurified via flash column chromatography (SiO2, hexane:ethyl acetate 100/0-50/50)

Sources & evidence

ORD record
ord-24cb02f2996c42519295064cf157ef53
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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