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

HRID 250678Notes

Reaction equation

HRID 250678 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-6179017833d047ee956c2f00ba2d05bc
Source dataset
uspto-grants-2011_01
Patent number
US07863288B2

Reaction notes

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