Lithium triethylborohydride → HCID 67241020, compound

HRID 335776Notes

Reaction equation

HRID 335776 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:21](=[CH:22][CH:23]=1)[O:20][C:7]1=[N:8][CH:9]=[C:10]([O:12][CH2:13][C:14]([O:18][CH3:19])([CH3:17])[CH2:15]I)[CH:11]=[C:6]1[C:5]2=[O:24].[CH3:25][Mg]Cl.[Li+].[B-](CC)(CC)CC>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:21](=[CH:22][CH:23]=1)[O:20][C:7]1=[N:8][CH:9]=[C:10]([O:12][CH2:13][C:14]([O:18][CH3:19])([CH3:17])[CH3:15])[CH:11]=[C:6]1[C:5]2([CH3:25])[OH:24]

Participants

5

Reactant 3

HCID 23712863Lithium triethylborohydrideHCID 67240282HCID 67240282, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 67241020HCID 67241020, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-bromo-3-(3-iodo-2-methoxy-2-methylpropoxy)-5H-chromeno[2,3-b]pyridin-5-one (4.10 g, 8.13 mmol) in 100 mL THF was cooled to −40° C. and was treated with methylmagnesium chloride (5.42 mL, 16.27 mmol). After stirring for two hours, the reaction mixture was allowed to warm to room temperature and superhydride (40.7 mL, 40.7 mmol) was added. After stirring for an additional 2 hours the reaction mixture was cooled to 0° C. and was quenched with MeOH. The reaction mixture was poured into saturated NH4Cl solution and was extracted with EtOAc. The organics were washed with waer, brine, dried over MgSO4 and concentrated yielding 7-bromo-3-(2-methoxy-2-methylpropoxy)-5-methyl-5H-chromeno[2,3-b]pyridin-5-ol.

Workup

  1. stirringAfter stirring for an additional 2 hours the reaction mixture
  2. temperaturewas cooled to 0° C.
  3. customwas quenched with MeOH
  4. additionThe reaction mixture was poured into saturated NH4Cl solution
  5. extractionwas extracted with EtOAc
  6. washThe organics were washed with waer, brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-054b18872d454bf5905b5d32c811ecd2
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

Loading…