Sodium hydride → HCID 67238426, compound

HRID 1521708Notes

Reaction equation

HRID 1521708 reaction equation
[NH:1]1[C:5]2=[N:6][C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:15]([O:17][CH2:18][CH3:19])=[O:16].[H-].[Na+].[CH3:22][CH:23]1OS(=O)(=O)[N:26]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:25][CH2:24]1>CN(C=O)C>[C:34]([O:33][C:31]([NH:26][CH2:25][CH2:24][CH:23]([N:1]1[C:5]2=[N:6][C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:22])=[O:32])([CH3:37])([CH3:36])[CH3:35]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 67236396Diethyl 1H-pyrrolo[2,3-B]pyridine-2,6-dicarboxylate2×HCID 86682388Tert-butyl 6-methyl-1,2,3-oxathiazinane-3-carboxylate 2,2-dioxide

Product 1

HCID 67238426HCID 67238426, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of diethyl 1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate (Intermediate D, 1.00 g, 3.81 mmol) in DMF (15 mL) cooled to 0° C. is added 60% sodium hydride in mineral oil (168 mg, 4.19 mmol). The mixture is stirred at 0° C. for 20 min after which a solution of tert-butyl 6-methyl-1,2,3-oxathiazinane-3-carboxylate 2,2-dioxide (1.05 g, 4.19 mmol) in DMF (2 mL) is added. After being stirred overnight, the mixture is concentrated under reduced pressure and the residue is partitioned between ethyl acetate and saturated NaHCO3 solution. The layers are separated and the aqueous layer is further extracted with ethyl acetate. The combined organic phases are washed with brine, and are dried (Na2SO4). The solvent is removed in vacuo and the crude material is purified via flash column chromatography using a gradient elution of 0-30% ethyl acetate/heptanes to afford the title compound as a yellow oil (1.20 g, 73%). LCMS: 434.89 (M+H+).

Workup

  1. additionis added
  2. concentrationthe mixture is concentrated under reduced pressure
  3. customthe residue is partitioned between ethyl acetate and saturated NaHCO3 solution
  4. customThe layers are separated
  5. extractionthe aqueous layer is further extracted with ethyl acetate
  6. washThe combined organic phases are washed with brine
  7. dry with materialare dried (Na2SO4)
  8. customThe solvent is removed in vacuo
  9. customthe crude material is purified via flash column chromatography
  10. washa gradient elution of 0-30% ethyl acetate/heptanes

Sources & evidence

ORD record
ord-c612bdc7aa7c43efbb62c80b29226a9a
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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