Sodium hydride → HCID 54751409, compound

HRID 1661496Notes

Reaction equation

HRID 1661496 reaction equation
[O:1]1CCC[O:3][CH:2]1[CH2:7][CH2:8][C:9]([C:11]1[C:16](=[O:17])[N:15]([CH3:18])[C:14]2[CH:19]=[C:20]([Br:22])[S:21][C:13]=2[C:12]=1[OH:23])=[O:10].BrC1SC2C(O)=C(C(OCC)=O)C(=O)N(C)C=2C=1.BrC1SC(C(OC)=O)=C(NC)C=1.[H-].[Na+]>C1COCC1>[Br:22][C:20]1[S:21][C:13]2[C:12]([OH:23])=[C:11]([C:9](=[O:10])[CH2:8][CH2:7][C:2]([OH:3])=[O:1])[C:16](=[O:17])[N:15]([CH3:18])[C:14]=2[CH:19]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 57744890HCID 57744890, compoundHCID 67428955HCID 67428955, compoundHCID 67429737HCID 67429737, compound

Product 1

HCID 54751409HCID 54751409, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

6-(3-(1,3-Dioxan-2-yl)propanoyl)-2-bromo-7-hydroxy-4-methylthieno[3,2-b]pyridin-5(4H)-one. To ethyl 2-bromo-7-hydroxy-4-methyl-5-oxo-4,5-dihydrothieno[3,2-b]pyridine-6-carboxylate (800 mg, 2408 μmol, prepared in a manner similar to that described in Method 7 using methyl 5-bromo-3-(methylamino)thiophene-2-carboxylate (Method 6(b))) was added THF (24 mL) and sodium hydride (60% in oil; 963 mg, 24084 μmol). The resulting mixture was stirred for 1 hour at ambient temperature. 2-[2-(1,3-Dioxanyl)]ethylmagnesium bromide in THF (4.81 mL, 2408 μmol) was then added dropwise at ambient temperature, and the resulting mixture was stirred for 3 hours before it was quenched with water, acidified with 5 N HCl, filtered, washed with water, and dried in a vacuum oven. The crude product was purified via HPLC to give the title compound.

Workup

  1. stirringthe resulting mixture was stirred for 3 hours before it
  2. customwas quenched with water
  3. filtrationfiltered
  4. washwashed with water
  5. customdried in a vacuum oven
  6. customThe crude product was purified via HPLC

Sources & evidence

ORD record
ord-3fddad7a0ca141ccacacbac722c81296
Source dataset
uspto-grants-2011_10
Patent number
US08030346B2

Reaction notes

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