Water → HCID 89924150, compound

HRID 1752645Notes

Reaction equation

HRID 1752645 reaction equation
[I:1][C:2]1[C:7]([C:8](OCC)=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]2[N:14]([CH3:17])[CH:15]=[CH:16][C:3]=12.CC(C[AlH]CC(C)C)C.O.[OH-].[Na+]>ClCCl>[I:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([CH3:13])[N:5]=[C:4]2[N:14]([CH3:17])[CH:15]=[CH:16][C:3]=12

Participants

6

Reactant 4

HCID 962Water2×HCID 14487Diisobutylaluminum hydrideHCID 14798Sodium HydroxideHCID 89923718Ethyl 4-iodo-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

Product 1

HCID 89924150HCID 89924150, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A −78° C. solution of ethyl 4-iodo-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate in dichloromethane (DCM) (150 mL) was treated dropwise with DIBAL-H (128 mL, 128 mmol) and warmed to ambient temperature. After 30 min, the reaction mixture was cooled to 0° C. and treated sequentially with water (5.1 mL), 15% NaOH (5.1 mL) and finally water (12.8 mL) with a 10 minute delay in between each addition. The fine suspension was then filtered through a pad of celite and washed with ethyl acetate 3×. The filtrate was concentrated in vacuo to afford (4-iodo-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanol (12.4 g, 41.0 mmol, 96% yield) as a yellow solid.

Workup

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. additionin between each addition
  3. filtrationThe fine suspension was then filtered through a pad of celite
  4. washwashed with ethyl acetate 3×
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-48b8abc85ce340f397fa3a9388a11a8d
Source dataset
uspto-grants-2015_10
Patent number
US09163023B2

Reaction notes

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