Sodium Bicarbonate → HCID 59497564, compound

HRID 1747448Notes

Reaction equation

HRID 1747448 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([Br:15])[CH:8]=[C:9]2[C:13]=1[N:12]([CH3:14])[CH:11]=[CH:10]2)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O-])(O)=O.[Na+]>CCOCC>[Br:15][C:7]1[CH:8]=[C:9]2[C:13](=[C:5]([CH2:3][OH:2])[CH:6]=1)[N:12]([CH3:14])[CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 59497666HCID 59497666, compound

Product 1

HCID 59497564HCID 59497564, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5-Bromo-1-methyl-1H-indole-7-carboxylic acid methyl ester (260 mg, 0.97 mmol) in Et2O (50 mL) was added LAH (40.5 mg, 1.1 mmol) at 0 C under nitrogen atmosphere. The solution was warmed to room temperature. Sat. NaHCO3 was added and the solution was extracted with EtOAc. The combined organic layer was dried with MgSO4 and was filtered. The filtrate was concentrated and the residue was purified by CombiFlash with 50% EtOAc in Hexane as the eluent to afford the desirable product (5-Bromo-1-methyl-1H-indol-7-yl)-methanol (200 mg, 86%) as colorless oil.

Workup

  1. extractionthe solution was extracted with EtOAc
  2. dry with materialThe combined organic layer was dried with MgSO4
  3. filtrationwas filtered
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by CombiFlash with 50% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-c14d1c9fb18541eca2b7113c7ea73c33
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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