Aluminium lithium hydride → 3-Bromo-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-methanol

HRID 1506013Notes

Reaction equation

HRID 1506013 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[N:19]=[CH:18][C:17]2[NH:16][C:15]3[N:20]=[CH:21][C:22]([Br:24])=[CH:23][C:14]=3[C:13]=2[CH:12]=1)=O>C1COCC1>[Br:24][C:22]1[CH:21]=[N:20][C:15]2[NH:16][C:17]3[CH:18]=[N:19][C:11]([CH2:9][OH:8])=[CH:12][C:13]=3[C:14]=2[CH:23]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58266719Methyl 3-bromo-9H-pyrrolo[2,3-b:5,4-c']dipyridine-6-carboxylate

Product 1

HCID 582664323-Bromo-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (1M solution in THF, 16.3 mL, 16.3 mmol) was added dropwise to a suspension of 3-bromo-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carboxylic acid methyl ester (500 mg, 1.63 mmol) in THF (10 mL). After 10 minutes the reaction mixture was quenched with a solution of saturated ammonium chloride, diluted with DCM and water and the solid removed by filtration. The layers of the resultant filtrate were separated and the aqueous phase was further extracted with DCM. The combined organic layer was concentrated in vacuo and purified by flash chromatography (silica, 1-15% methanol in DCM).

Workup

  1. customAfter 10 minutes the reaction mixture was quenched with a solution of saturated ammonium chloride
  2. additiondiluted with DCM and water
  3. customthe solid removed by filtration
  4. customThe layers of the resultant filtrate were separated
  5. extractionthe aqueous phase was further extracted with DCM
  6. concentrationThe combined organic layer was concentrated in vacuo
  7. custompurified by flash chromatography (silica, 1-15% methanol in DCM)

Sources & evidence

ORD record
ord-1e54a3078b8c40f2bc26ba526a2957c1
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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