3-Iodo-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine → [5-(4-chloro-benzyloxy)-4-methoxy-pyridin-2-yl]-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol

HRID 1261109Notes

Reaction equation

HRID 1261109 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:3]=1.C([Mg]Cl)(C)C.[Cl:26][C:27]1[CH:44]=[CH:43][C:30]([CH2:31][O:32][C:33]2[C:34]([O:41][CH3:42])=[CH:35][C:36]([CH:39]=[O:40])=[N:37][CH:38]=2)=[CH:29][CH:28]=1>O1CCCC1>[Cl:26][C:27]1[CH:44]=[CH:43][C:30]([CH2:31][O:32][C:33]2[C:34]([O:41][CH3:42])=[CH:35][C:36]([CH:39]([C:2]3[C:10]4[C:5](=[N:6][CH:7]=[CH:8][CH:9]=4)[N:4]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:3]=3)[OH:40])=[N:37][CH:38]=2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 242292273-Iodo-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridineHCID 580874295-(4-Chloro-benzyloxy)-4-methoxy-pyridine-2-carbaldehydeHCID 178418918HCID 178418918, compound

Product 1

HCID 58087829[5-(4-chloro-benzyloxy)-4-methoxy-pyridin-2-yl]-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-20 °C

Procedure

3-Iodo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (635, 180 mg, 0.450 mmol) was dissolved in tetrahydrofuran (2.5 mL) and the reaction was cooled to −20° C. under an atmosphere of nitrogen. Isopropylmagnesium chloride in tetrahydrofuran (2.00 M, 0.243 mL) was added. The reaction was stirred for 1 hour, during which the temperature rose to 0° C. The reaction was cooled to −20° C. and 5-(4-chloro-benzyloxy)-4-methoxy-pyridine-2-carbaldehyde (641, 80.0 mg, 0.288 mmol) in tetrahydrofuran (0.75 mL) was added. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was quenched with methanol and adsorbed onto silica, then purified by silica gel chromatography, methanol: dichloromethane, to provide the desired product, (642, 94 mg, 59%). 1H-NMR was consistent with the desired compound. MS (ESI) [M+H+]+=552.4, 554.4, 555.4.

Workup

  1. customrose to 0° C
  2. temperatureThe reaction was cooled to −20° C.
  3. temperatureto warm to room temperature
  4. stirringstirred overnight
  5. customThe reaction was quenched with methanol
  6. custompurified by silica gel chromatography, methanol

Sources & evidence

ORD record
ord-457d3a0415d440e2aa313a825ab4275b
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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