1H-Pyrrolo[2,3-B]pyridine, 1-[(1,1-dimethylethyl)dimethylsilyl]-3-iodo- → [1-(tert-Butyl-dimethyl-silanyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-4-[1-(4-chloro-phenyl)-ethoxy]-3-methoxy-phenyl-methanol

HRID 1098472Notes

Reaction equation

HRID 1098472 reaction equation
[C:1]([Si:5]([CH3:17])([CH3:16])[N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[C:8](I)=[CH:7]1)([CH3:4])([CH3:3])[CH3:2].C([Mg]Cl)(C)C.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]([O:32][C:33]2[CH:40]=[CH:39][C:36]([CH:37]=[O:38])=[CH:35][C:34]=2[O:41][CH3:42])[CH3:31])=[CH:26][CH:25]=1>O1CCCC1>[C:1]([Si:5]([CH3:17])([CH3:16])[N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[C:8]([CH:37]([C:36]2[CH:39]=[CH:40][C:33]([O:32][CH:30]([C:27]3[CH:28]=[CH:29][C:24]([Cl:23])=[CH:25][CH:26]=3)[CH3:31])=[C:34]([O:41][CH3:42])[CH:35]=2)[OH:38])=[CH:7]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 497589601H-Pyrrolo[2,3-B]pyridine, 1-[(1,1-dimethylethyl)dimethylsilyl]-3-iodo-HCID 580868174-[1-(4-Chloro-phenyl)-ethoxy]-3-methoxy-benzaldehydeHCID 178418918HCID 178418918, compound

Product 1

HCID 58086672[1-(tert-Butyl-dimethyl-silanyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-4-[1-(4-chloro-phenyl)-ethoxy]-3-methoxy-phenyl-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-20 °C

Procedure

1-(tert-Butyl-dimethyl-silanyl)-3-iodo-1H-pyrrolo[2,3-b]pyridine (636, 647.0 mg, 1.81 mmol) was dissolved in tetrahydrofuran (10.0 mL) at −20° C. under an atmosphere of nitrogen. Isopropylmagnesium chloride in tetrahydrofuran (2.0 M, 0.98 mL) was added to the reaction. The reaction was stirred for 1 hour, during which the temperature rose to 0° C. The reaction was cooled to −20° C. and 4-[1-(4-chloro-phenyl)-ethoxy]-3-methoxy-benzaldehyde(644, 420 mg, 1.4 mmol) in tetrahydrofuran (3.00 mL) was added. The reaction was stirred for 2 hours during which time the temperature rose to 10° C. The reaction was quenched with methanol and adsorbed onto silica, then purified by silica gel chromatography, ethyl acetate:hexanes, to provide the desired compound, (645, 463 mg, 61%). 1H-NMR was consistent with the desired compound.

Workup

  1. customrose to 0° C
  2. stirringThe reaction was stirred for 2 hours during which time the temperature
  3. customrose to 10° C
  4. customThe reaction was quenched with methanol
  5. custompurified by silica gel chromatography, ethyl acetate

Sources & evidence

ORD record
ord-04bba749f45d414aa501d64903488815
Source dataset
uspto-grants-2012_03
Patent number
US08143271B2

Reaction notes

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