Dichloromethane → HCID 58382494, compound

HRID 1628100Notes

Reaction equation

HRID 1628100 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[OH:9])=[CH:6][N:5]=[C:4]2[NH:18][CH:19]=[CH:20][C:3]=12.C(Cl)Cl.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>O>[Cl:1][C:2]1[C:7]([C:8]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)=[O:9])=[CH:6][N:5]=[C:4]2[NH:18][CH:19]=[CH:20][C:3]=12

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 58382125HCID 58382125, compound

Product 1

HCID 58382494HCID 58382494, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (4-chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)(4-methoxyphenyl)methanol (2.34 g, 8.10 mmol, prepared using S from Preparation #1, Step B with (4-(2-methyl-1,3-dioxolan-2-yl)phenyl)magnesium bromide [NOVEL]) and DCM (30 mL) was added Dess-Martin periodinane (3.44 g, 8.10 mmol). The mixture was stirred at rt for about 3 h. Water was added (15 mL) and the resulting precipitate was collected by filtration and dried under reduced pressure at about 60° C. for about 2 h to give (4-chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)(4-methoxyphenyl)methanone (2.14 g, 92%): LC/MS (Table 2, Method b) Rt=2.17 min.; MS m/z: 287 (M+H)+.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. customdried under reduced pressure at about 60° C. for about 2 h

Sources & evidence

ORD record
ord-e865560c2081451dbf1296650d8af105
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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