Sodium hydride → HCID 57586716, compound

HRID 1097738Notes

Reaction equation

HRID 1097738 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.[CH2:11]([N:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][N:26]=2)[C:21](Cl)=[CH:20][C:19]1=[O:29])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C=O)C>[CH2:11]([N:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][N:26]=2)[C:21]([S:10][C:7]2[CH:8]=[CH:9][C:4]([Br:3])=[CH:5][CH:6]=2)=[CH:20][C:19]1=[O:29])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 660494-BromothiophenolHCID 121630381-Benzyl-4-chloro-1,8-naphthyridin-2(1H)-one

Product 1

HCID 57586716HCID 57586716, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of NaH (24 mg, 1 mmol) in DMF (4 mL) was added 4-bromobenzenethiol (189 mg, 1 mmol) at 0° C. After being stirred at rt for 10 min, a solution of 1-benzyl-4-chloro-1H-[1,8]naphthyridin-2-one (135 mg, 0.5 mmol) in DMF (1 mL) was introduced at rt. The reaction was quenched by adding water followed by extracting with EtOAc. The organic layer was washed with brine and dried over Na2SO4. Column chromatography of the concentrated residue gave 210 mg of product (yield: 100%): 1H NMR (500 MHz, CDCl3) δ 8.63 (d, J=5.0 Hz, 1H), 8.21 (d, J=8.0 Hz, 1H), 7.62 (d, J=8.5 Hz, 2H), 7.46 (d, J=7.5 Hz, 2H), 7.43 (d, J=8.5 Hz, 2H), 7.25 (t, J=7.5 Hz, 2H), 7.21 (dd, J=8.0, 5.0 Hz, 1H), 7.20 (t, J=8.0 Hz, 1H), 6.10 (s, 1H), 5.70 (s, 2H); 13C NMR (125 MHz, CDCl3) 161.65, 150.77, 149.42, 148.87, 137.85, 137.46, 133.78, 132.97, 128.82, 128.47, 127.38, 126.81, 125.50, 118.09, 117.66, 114.65, 44.20; LCMS (EI) m/z 422.8 (M+), 424.8.

Workup

  1. customThe reaction was quenched
  2. additionby adding water
  3. extractionby extracting with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-f988686282d247aea6554ae9f8daa93c
Source dataset
uspto-grants-2012_03
Patent number
US08143276B2

Reaction notes

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