Methanol → [4-(1H-benzoimidazol-2-ylmethoxy)-2-chloro-5-methoxy-phenyl]-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol

HRID 253456Notes

Reaction equation

HRID 253456 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[NH:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[CH2:20][O:21][C:22]1[C:29]([O:30][CH3:31])=[CH:28][C:25]([CH:26]=[O:27])=[C:24]([Cl:32])[CH:23]=1.CO.[OH-].[K+]>>[NH:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[CH2:20][O:21][C:22]1[C:29]([O:30][CH3:31])=[CH:28][C:25]([CH:26]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[NH:8][CH:9]=2)[OH:27])=[C:24]([Cl:32])[CH:23]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 242292135-Chloro-1H-pyrrolo[2,3-b]pyridineHCID 598038904-(1H-benzoimidazol-2-ylmethoxy)-2-chloro-5-methoxy-benzaldehyde

Product 1

HCID 59803826[4-(1H-benzoimidazol-2-ylmethoxy)-2-chloro-5-methoxy-phenyl]-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol

Procedure

5-Chloro-1H-pyrrolo[2,3-b]pyridine (4, 783.9 mg, 0.005138 mol, prepared as described in Example 4) and 4-(H-benzoimidazol-2-ylmethoxy)-2-chloro-5-methoxy-benzaldehyde (137, 1.79 g, 0.00565 mmol) were combined in methanol (100 mL, 2 mol) and potassium hydroxide (2.88 g, 0.0514 mol) was added. The reaction was stirred at room temperature overnight. The reaction was adsorbed onto silica and purified by silica gel column chromatography, eluting with 1-15% methanol:dichloromethane to provide the desired compound as a yellow oil, which was redissolved in 200 mL of 25% ethyl acetate:hexanes and concentrated to provide a yellow solid (138, 1.2 g, 50%). MS (ESI) [M+H+]+=469.1, 471.1.

Workup

  1. custompurified by silica gel column chromatography
  2. washeluting with 1-15% methanol

Sources & evidence

ORD record
ord-1545b7a9f05e43b9980b36e159deb55d
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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