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

HRID 1098495Notes

Reaction equation

HRID 1098495 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-3ec83c5c412647eaa46547814555328c
Source dataset
uspto-grants-2012_03
Patent number
US08143271B2

Reaction notes

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