Water → 4-(2-Pyrrolidin-1-yl-pyridine-4-sulfonyl)-phenylamine

HRID 1603564Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[C:4]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[N:3]=1.[Li]CCCC.O>O1CCCC1.CCCCCC>[N:18]1([C:4]2[CH:5]=[C:6]([S:8]([C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=3)(=[O:10])=[O:9])[CH:7]=[CH:2][N:3]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

Conditions

Temperature: -40 °C

Procedure

10.0 g (0.026 Mol) 4-(2-Bromo-6-pyrrolidin-1-yl-pyridine-4-sulfonyl)-phenylamine were dissolved in tetrahydrofuran (200 ml), cooled at -40° C. and 33 ml (0.053 Mol) nBuLi in hexane were added. The reaction mixture was stirred at -15° C. for 1 h. Then water (10 ml) was added, the mixture was extracted with ethylacetate, the organic phase was washed with water and brine and dried over Na2SO4. After chromatography on SiO2 with ethyl acetate hexan 1:1 and drying in a high vacuum, it was obtained 3.6 g (45%) of 4-(2-pyrrolidin-1-yl-pyridine-4-sulfonyl) -phenylamine as light yellow cristals; mp.: 186-187° C.

Workup

extractionthe mixture was extracted with ethylacetate
washthe organic phase was washed with water and brine
dry with materialdried over Na2SO4
dry with materialAfter chromatography on SiO2 with ethyl acetate hexan 1:1 and drying in a high vacuum

Sources & evidence

ORD record: ord-ade67386b37d42cba3114e5f54ba931f
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990105

Reaction notes

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