Sodium Azide → 3-(2-azidoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1777583Notes

Reaction equation

Br[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[N:8][CH:9]=[C:10]([Cl:13])[CH:11]=2)[NH:6][C:5]=1[Si:14]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:15][CH3:16].[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C=O)C>[N:21]([CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[N:8][CH:9]=[C:10]([Cl:13])[CH:11]=2)[NH:6][C:5]=1[Si:14]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:15][CH3:16])=[N+:22]=[N-:23]

Participants

Conditions

Temperature: 80 °C

Procedure

The mixture of 3-(2-bromoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridine (1.05 g; 2.81 mmol) and sodium azide (0.547 g; 8.43 mmol) in DMF (8 mL) was stirred for 18 hours at 80° C. and was concentrated in vacuo. The residue was partitioned between water and dichloromethane. After separation, the dichloromethane solution was dried over magnesium sulfate and was evaporated to give 0.943 g (100%) of 3-(2-azidoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridine as a solid.

Workup

concentrationwas concentrated in vacuo
customThe residue was partitioned between water and dichloromethane
customAfter separation
dry with materialthe dichloromethane solution was dried over magnesium sulfate
customwas evaporated

Sources & evidence

ORD record: ord-c3674a54c9ef402c9859084e7d5c8db2
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266832B2

Reaction notes

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