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

HRID 1261134Notes

Reaction equation

HRID 1261134 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-97f20c974b45495dac88e25596f21029
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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