HCID 89924150, compound → HCID 89923953, compound

HRID 1752646Notes

Reaction equation

HRID 1752646 reaction equation
[I:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([CH3:10])[N:5]=[C:4]2[N:11]([CH3:14])[CH:12]=[CH:13][C:3]=12.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>ClCCl>[I:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([CH3:10])[N:5]=[C:4]2[N:11]([CH3:14])[CH:12]=[CH:13][C:3]=12

Participants

4

Reactant 2

HCID 89924150HCID 89924150, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 89923953HCID 89923953, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (4-iodo-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanol in dichloromethane (DCM) (300 mL) was treated with PCC (11.96 g, 55.5 mmol) and Celite™ (17 g) in one portion. After 3 h, the mixture was diluted with DCM (100 mL) and filtered through a pad of celite and washed with DCM/ethyl acetate (10:1). The filtrate was concentrated in vacuo to afford the title compound (10.8 g, 36.0 mmol, 84% yield) as a yellow solid: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.88 (s, 3H) 3.88 (s, 3H) 6.48 (d, J=3.52 Hz, 1H) 7.22 (d, J=3.52 Hz, 1H) 10.36 (s, 1H). LC/MS (m/z) ES+=301 (M+1)+

Workup

  1. filtrationfiltered through a pad of celite
  2. washwashed with DCM/ethyl acetate (10:1)
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-253e5aa9e9504b19bd4027aac2a456aa
Source dataset
uspto-grants-2015_10
Patent number
US09163023B2

Reaction notes

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