1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-(Azidomethyl)thieno[3,2-c]pyridine

HRID 876768Notes

Reaction equation

[S:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=[C:2]1[CH2:10]O.C1C=CC(P([N:26]=[N+:27]=[N-:28])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1>C1COCC1>[N:26]([CH2:10][C:2]1[S:1][C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=1)=[N+:27]=[N-:28]

Participants

Conditions

Temperature: 0 °C

Procedure

To a flame-dried round-bottomed flask containing thieno[3,2-c]pyridin-2-ylmethanol (D-3) (3.2 g, 19.4 mmol) was added DPPA (8 g, 6.26 mL, 29.1 mmol) in THF (50 mL). The reaction mixture was stirred for 5 mins and cooled to 0° C., followed by adding DBU (4.43 g, 4 mL, 29.1 mmol) via syringe. The mixture was allowed to stir at reflux overnight. The reaction was then partitioned between water and ethyl ether. The aqueous layer was extracted with ethyl ether. The combined organic layers were washed with brine, dried over Na2SO4, concentrated, and purified by chromatography to afford the product (3.27 g). MS (m/z): 191 (M+1)+.

Workup

stirringto stir
temperatureat reflux overnight
customThe reaction was then partitioned between water and ethyl ether
extractionThe aqueous layer was extracted with ethyl ether
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated
custompurified by chromatography

Sources & evidence

ORD record: ord-4938c555883547edaccdfde847c79c0d
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987269B2

Reaction notes

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