Lithium triethylborohydride → HCID 67241020, compound

HRID 1970370Notes

Reaction equation

HRID 1970370 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 water, 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 water, brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-46104b06e584485d800b33001fc1d4b4
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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