Iodine → HCID 66738218, compound

HRID 561019Notes

Reaction equation

[C:1]([O:5][C:6](=[O:17])[NH:7][CH:8]([C:10]1[CH:11]=[N:12][C:13]([F:16])=[CH:14][CH:15]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].C([Li])(C)(C)C.[I:23]I.O>C1COCC1>[C:1]([O:5][C:6](=[O:17])[NH:7][CH:8]([C:10]1[CH:11]=[N:12][C:13]([F:16])=[CH:14][C:15]=1[I:23])[CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: -78 °C

Procedure

Add a solution of [1-(6-fluoro-pyridin-3-yl)-ethyl]-carbamic acid tert-butyl ester (9.3 g, 38.8 mmol) in dry THF (90 mL) into tert-butyllithium (68.4 mL, 116.3 mmol, 1.7 M solution in pentane) in dry THF (70 mL) over 15 min under N2 at −78° C. Stir at −78° C. for 1 hour. Add a solution of iodine (14.8 g, 58.2 mmol) in dry THF (90 mL) over 15 min. Stir at −78° C. for 2 hours. Warm up to 0° C. Add water. Warm up to room temperature. Extract with ethyl acetate. Wash the organic layer with Na2CO3 solution, water and saturated aqueous sodium chloride, and dry over MgSO4. After filtration, concentrate and purify the crude by flash chromatography (5% to 20% ethyl acetate/hexane). Afford the desired product [1-(6-fluoro-4-iodo-pyridin-3-yl)-ethyl]-carbamic acid tert-butyl ester (2.8 g, 20%), MS (ES) m/z 367 [M+1]+.

Workup

stirringStir at −78° C. for 2 hours
temperatureWarm up to 0° C
temperatureWarm up to room temperature
extractionExtract with ethyl acetate
washWash the organic layer with Na2CO3 solution, water and saturated aqueous sodium chloride
dry with materialdry over MgSO4
filtrationAfter filtration
concentrationconcentrate
custompurify the crude by flash chromatography (5% to 20% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-8dccd7a801c64caca606d56baf877709
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063212B2

Reaction notes

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