furo[2,3-b]pyridine-5-carbaldehyde → HCID 68415383, compound

HRID 220269Notes

Reaction equation

HRID 220269 reaction equation
[Cl-].[CH3:2][NH:3][C:4]([CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:5].[Li]CCCC.[O:31]1[C:35]2=[N:36][CH:37]=[C:38]([CH:40]=O)[CH:39]=[C:34]2[CH:33]=[CH:32]1>C1COCC1>[O:31]1[C:35]2=[N:36][CH:37]=[C:38]([CH:40]=[CH:6][C:4]([NH:3][CH3:2])=[O:5])[CH:39]=[C:34]2[CH:33]=[CH:32]1

Participants

5

Reactant 3

HCID 10749327furo[2,3-b]pyridine-5-carbaldehydeHCID 85777853HCID 85777853, compoundHCID 178418339Butyllithium

Product 1

HCID 68415383HCID 68415383, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.25 g of methylcarbamoylmethyl-triphenyl-phosphonium chloride (J. Med. Chem. 2003, 46, 399) in 1 ml of THF was added 0.88 ml of n-BuLi (1.6M) at −60° C. After stirring for 1 h at −60° C. a solution of 0.1 g of furo[2,3-b]pyridine-5-carbaldehyde in 1 ml of THF was added and the resulting reaction mixture was stirred for 5 h reaching slowly rt. The reaction mixture was poured over ice. The organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo. Purification by CC using EtOAc as eluant yielded 0.13 g of 3-furo[2,3-b]pyridin-5-yl-N-methyl-acrylamide as a mixture of E/Z isomers.

Workup

  1. additionwas added
  2. customthe resulting reaction mixture
  3. customreaching slowly rt
  4. additionThe reaction mixture was poured over ice
  5. washThe organic phase was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification by CC

Sources & evidence

ORD record
ord-3f5be8ed752d43c9a7e44daed6b1989c
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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