Ethyl orthoformate → 3-(3-ethoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-6-iodo-3H-imidazo[4,5-b]pyridine

HRID 706473Notes

Reaction equation

HRID 706473 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][C:19]=1[O:20][CH2:21][C:22]1[CH:23]=[N:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)[CH2:7][NH:8][C:9]1[C:14]([NH2:15])=[CH:13][C:12]([I:16])=[CH:11][N:10]=1)[CH3:2].[CH:30](OCC)(OCC)OCC>C(O)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][C:19]=1[O:20][CH2:21][C:22]1[CH:23]=[N:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)[CH2:7][N:8]1[C:9]2=[N:10][CH:11]=[C:12]([I:16])[CH:13]=[C:14]2[N:15]=[CH:30]1)[CH3:2]

Participants

5

Reactant 2

HCID 31214Ethyl orthoformateHCID 118141894N2-(3-ethoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-5-iodopyridine-2,3-diamine

Product 1

HCID 1181141063-(3-ethoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-6-iodo-3H-imidazo[4,5-b]pyridineYield 61.4%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 702EthanolSolvent

Procedure

To a stirred suspension of N2-(3-ethoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-5-iodopyridine-2,3-diamine (3.99 g, 7.88 mmol) in ethanol (50 mL) was added triethyl orthoformate (2.67 g, 18.02 mmol) and p-toluenesulfonic acid monohydrate (0.075 g, 0.39 mmol). As the mixture was heated to reflux, a brown solution was obtained. After 30 min, the mixture was allowed to cool to room temperature, resulting in the formation of a precipitate. The solids were isolated by filtration, washed with ethanol, and dried to provide 2.50 g (61%) of 3-(3-ethoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-6-iodo-3H-imidazo[4,5-b]pyridine as a tan solid.

Workup

  1. temperatureAs the mixture was heated
  2. temperatureto reflux
  3. customa brown solution was obtained
  4. customresulting in the formation of a precipitate
  5. customThe solids were isolated by filtration
  6. washwashed with ethanol
  7. customdried

Sources & evidence

ORD record
ord-07ce8b9ff06349babe98e03ad4b398d3
Source dataset
uspto-grants-2015_11
Patent number
US09174986B2

Reaction notes

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