2-Chloroethanol → HCID 68704610, compound

HRID 2240091Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([CH2:15][OH:16])=[CH:12][CH:13]=2)[C:8]([S:17]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[N:7]1.C(N(C(C)C)CC)(C)C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[Cl:57][CH2:58][CH2:59]O>C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([CH2:15][O:16][CH2:59][CH2:58][Cl:57])=[CH:12][CH:13]=2)[C:8]([S:17]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[N:7]1

Participants

Conditions

Temperature: -20 °C

Procedure

[1-(3-Chlorobenzyl)-3-(1-naphthylsulfonyl)-1H-indazol-5-yl]-methanol (0.18 g, 0.4 mmol) and diisopropyl ethyl amine (1 mmol) in methylene chloride were treated at −20° C. with trifluoromethanesulfonic anhydride (0.14 g, 0.5 mmol). After stirring for 30 min an excess of 2-chloroethanol (2 mmol) was added and the mixture stirred for additional 2 hrs at −20° C. and at room temperature for 12 hrs. The reaction mixture was diluted with water, extracted with ethyl acetate and after evaporation of solvent, chromatographed on silica gel using 40% ethyl acetate/hexane as an eluent to afford the target material (0.08 g, 0.16 mmoles).

Workup

additionwas added
extractionextracted with ethyl acetate
customafter evaporation of solvent
customchromatographed on silica gel using 40% ethyl acetate/hexane as an eluent

Sources & evidence

ORD record: ord-7d26724d95344e398606e67cd977366d
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723329B2

Reaction notes

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