Diisobutylaluminum hydride → HCID 90093910, compound

HRID 1753074Notes

Reaction equation

HRID 1753074 reaction equation
C[O:2][C:3](=O)[C:4]([N:7]1[C:15]2[C:14]([F:16])=[CH:13][N:12]=[CH:11][C:10]=2[C:9]([I:17])=[CH:8]1)([CH3:6])[CH3:5].CC(C[AlH]CC(C)C)C>C1COCC1>[F:16][C:14]1[C:15]2[N:7]([C:4]([CH3:5])([CH3:6])[CH2:3][OH:2])[CH:8]=[C:9]([I:17])[C:10]=2[CH:11]=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 90093877HCID 90093877, compound

Product 1

HCID 90093910HCID 90093910, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(7-Fluoro-3-iodo-pyrrolo[3,2-c]pyridin-1-yl)-2-methyl-propionic acid methyl ester (Preparation 71, 500 mg, 1.38 mmol) was taken in dry THF (3 mL) and DIBAL-H (25% solution in toluene, 2 mL, 3.03 mmol) was added drop wise at 0° C. and stirred at the same temperature for 2 hours. The reaction was quenched with MeOH, water, 2N HCl at 0° C. and stirred for 15 minutes before being diluted with EtOAc and water. The organic layer was separated and washed with brine, dried over sodium sulphate and evaporated in vacuo to obtain the title compound (65%) that was used in the next step directly without any further purification.

Workup

  1. customThe reaction was quenched with MeOH, water, 2N HCl at 0° C.
  2. stirringstirred for 15 minutes
  3. additionbefore being diluted with EtOAc and water
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulphate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-6a31f9f21b7749028f3e9ea2929630fd
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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