Cyanomethylenetributylphosphorane → 4-fluoro-N-(5-isopropylpyridin-2-yl)-N-(oxetan-3-ylmethyl)benzenesulfonamide

HRID 594143Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[O:21]1[CH2:24][CH:23]([CH2:25]O)[CH2:22]1.C(P(CCCC)(CCCC)=CC#N)CCC>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][N:13]=2)[CH2:25][CH:23]2[CH2:24][O:21][CH2:22]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 4-fluoro-N-(5-isopropylpyridin-2-yl)benzenesulfonamide (100 mg, 0.340 mmol) and oxetan-3-ylmethanol (20.95 mg, 0.238 mmol) in toluene (1.5 mL) stirred in air at room temperature was added a solution of 2-(tributylphosphoranylidene)acetonitrile (82 mg, 0.340 mmol) in toluene (0.5 mL). The reaction mixture was stirred at 20° C. for 16 hours. Additional 2-(tributylphosphoranylidene)acetonitrile (82 mg, 0.340 mmol) and oxetan-3-ylmethanol (20.95 mg, 0.238 mmol) were added and the solution stirred for a further 24 hours. The reaction solution was then purified on an aminopropyl (NH2) solid phase extraction (SPE) cartridge eluting with a 0-50% ethyl acetate-cyclohexane gradient, to give the title product (63 mg) as a colourless gum. LCMS (2 min, formic) Rt 1.12 min, m/z (ES+) 365 (M+H).

Workup

stirringthe solution stirred for a further 24 hours
customThe reaction solution was then purified on an aminopropyl (NH2) solid phase extraction (SPE) cartridge
washeluting with a 0-50% ethyl acetate-cyclohexane gradient

Sources & evidence

ORD record: ord-44033662bae34a65a637c3d5f025314c
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242972B2

Reaction notes

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