Sodium hydride → HCID 67436158, compound

HRID 1663407Notes

Reaction equation

HRID 1663407 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[CH3:9][N:10]([CH3:39])[C:11]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:24]=[C:23]3[O:25][C:26]4[C:31]([CH:32]([C:33](=[CH2:38])[C:34]([O:36][CH3:37])=[O:35])[C:22]3=[CH:21][CH:20]=2)=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:15][CH:14]=1)=[O:12]>CS(C)=O>[CH3:39][N:10]([CH3:9])[C:11]([C:13]1[CH:14]=[CH:15][C:16]([C:19]2[N:24]=[C:23]3[O:25][C:26]4[C:31]([CH:32]([C:33]5([C:34]([O:36][CH3:37])=[O:35])[CH2:4][CH2:38]5)[C:22]3=[CH:21][CH:20]=2)=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:17][CH:18]=1)=[O:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 67436917HCID 67436917, compound

Product 1

HCID 67436158HCID 67436158, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Sodium hydride (5.2 mg, 0.13 mmol, 60% in mineral oil) was added to a solution of trimethyl sulfoxonium iodide (28.7 mg, 0.13 mmol) in DMSO (1 mL) at room temperature. After 30 min at room temperature, the mixture was added to a solution of the product from Step 3 (45 mg, 0.109 mmol) in DMSO (1 mL). The resultant mixture was stirred at room temperature for 10 min and quenched with saturated NaHCO3 (1 mL). After addition of ethyl acetate (80 mL), the mixture was washed with water (2×10 mL), brine (10 mL), dried (MgSO4) and concentrated. The residue was purified by flash column chromatography (silica, 50-100% ethyl acetate in hexanes) to provide methyl 1-(2-(4-(dimethylcarbamoyl)phenyl)-5H-chromeno[2,3-b]pyridin-5-yl)cyclopropanecarboxylate (12 mg, 26%). MS (ES+) m/z: 429 (M+H).

Workup

  1. customquenched with saturated NaHCO3 (1 mL)
  2. additionAfter addition of ethyl acetate (80 mL)
  3. washthe mixture was washed with water (2×10 mL), brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (silica, 50-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-3cb8d3d78a3e43f5bcd1cee4090da1b6
Source dataset
uspto-grants-2011_10
Patent number
US08034940B2

Reaction notes

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