Isopropyl chloroformate → 1H-Pyrrolo[2,3-B]pyridine, 3-(chloromethyl)-1-[tris(1-methylethyl)silyl]-

HRID 1964982Notes

Reaction equation

HRID 1964982 reaction equation
CN(C)[CH2:3][C:4]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[N:6]([Si:13]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])[CH:5]=1.[Cl:24]C(OC(C)C)=O>C1(C)C=CC=CC=1>[Cl:24][CH2:3][C:4]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[N:6]([Si:13]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])[CH:5]=1

Participants

4

Reactant 2

HCID 7917Isopropyl chloroformateHCID 497589771H-Pyrrolo[2,3-B]pyridine-3-methanamine, N,N-dimethyl-1-[tris(1-methylethyl)silyl]-

Product 1

HCID 497589211H-Pyrrolo[2,3-B]pyridine, 3-(chloromethyl)-1-[tris(1-methylethyl)silyl]-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Dimethyl-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-amine 110 (1.25 g, 3.77 mmol) was added to toluene (20.0 mL) under an atmosphere of nitrogen at room temperature. Isopropyl chloroformate in toluene (1.0 M, 4.0 mL) was added. The reaction mixture was stirred at room temperature for 3 hours to provide a solution of 3-chloromethyl-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine.

Sources & evidence

ORD record
ord-b2a15b20043f4f408bda6b3d1f622ab3
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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