Sodium hydride → HCID 22241381, compound

HRID 892207Notes

Reaction equation

HRID 892207 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.C(=O)(O)[O-].[Na+].[OH:19][C:20]1[CH:21]=[C:22]([S:26][CH2:27][C:28]2[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[C:29]=2[C:30]([O:32][CH2:33][CH:34]([CH3:36])[CH3:35])=[O:31])[CH:23]=[CH:24][CH:25]=1.[H-].[Na+]>CN(C=O)C.C(OCC)C>[CH3:41][C:37]1[CH:38]=[CH:39][CH:40]=[C:28]([CH2:27][S:26][C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([O:19][CH2:3][C:4]3[CH:13]=[CH:12][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]=3)[CH:21]=2)[C:29]=1[C:30]([O:32][CH2:33][CH:34]([CH3:36])[CH3:35])=[O:31]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 22241506HCID 22241506, compound

Product 1

HCID 22241381HCID 22241381, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

The free base of 2-(chloromethyl)quinoline hydrochloride (148 mg, 0.69 mmol) is prepard by partioning the material between ethyl ether and sodium bicarbonate and drying the organic phase with magnesium sulfate. This material is then dissolved with isobutyl 2-[3-(hydroxy)-phenylsulfanylmethyl]-6-methyl-benzoate (220 mg, 0.67 mmol, example 83) in DMF (2 mL) at 0° C. and sodium hydride (60%, 27 mg 0.67 mmol) is added. The reaction is allowed to stir 16 h and is then partitioned between ethyl acetate and water. The organic phase is washed with water (3×), dried over magnesium sulfate, concentrated and purified by column chromatography (silica, 10% ethyl acetate in hexanes) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 8.19 (d, 1H), 8.08 (d, 1H), 7.83 (d, 1H), 7.74 (t, 1H), 7.63 (d, 1H), 7.55 (t, 1H), 7.18–7.07 (m, 4H), 6.99 (d, 1H), 6.89 (d, 1H), 6.82 (dd, 1H), 5.33 (s, 2H), 4.18 (s, 2H), 4.10 (d, 2H), 2.36 (s, 3H), 2.07–2.01 (m, 1H), 0.98 (d, 6H); MS (ESI) 472 (M+H)+.

Workup

  1. dry with materialdrying the organic phase with magnesium sulfate
  2. customis then partitioned between ethyl acetate and water
  3. washThe organic phase is washed with water (3×)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. custompurified by column chromatography (silica, 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-3629ad3bdc53454d955bc392efe65a38
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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