Triethylamine → HCID 67021370, compound

HRID 735472Notes

Reaction equation

[CH2:1]([N:8]1[C:16]([C:17]2[CH:18]=[C:19]([CH2:23][OH:24])[CH:20]=[CH:21][CH:22]=2)=[C:15]2[C:10]([C:11]([C:25]([F:28])([F:27])[F:26])=[CH:12][CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.CS(Cl)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+].[F:47][C:48]1[CH:53]=[CH:52][C:51]([F:54])=[CH:50][C:49]=1O>ClCCl>[CH2:1]([N:8]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][O:24][C:52]3[CH:53]=[C:48]([F:47])[CH:49]=[CH:50][C:51]=3[F:54])[CH:18]=2)=[C:15]2[C:10]([C:11]([C:25]([F:27])([F:28])[F:26])=[CH:12][CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -30 °C

Procedure

Thirty-eight milligrams (38 mg; 0.1 mmol) of [3-(2-benzyl-7-trifluoromethyl-2H-indazol-3-yl)-phenyl]-methanol (see preparation of Example 7) were dissolved in 1 ml of dichloromethane followed by the addition of 28 μl of Et3N (0.2 mmol). The mixture was cooled to −30° C. and 12 μl of MsCl were added. Stirring continued at 0° C. for 1.5 hours. To the resulting solution, 85 mg of Cs2CO3 (0.25 mmol) were added followed by the addition of 65 mg (0.5 mmol) of 2,5-difluorophenol. Then the reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched with 1M aq HCl and product was extracted with dichloromethane. Flash column chromatography (SiO2, dichloromethane/heptane, 1:1, as an eluant) afforded 2-benzyl-3-{3-[(2,5-difluorophenoxy)methyl]phenyl}-7-(trifluoromethyl)-2H-indazole in 41% yleld.

Workup

stirringThen the reaction mixture was stirred at room temperature overnight
customThe reaction mixture was quenched with 1M aq HCl and product
extractionwas extracted with dichloromethane

Sources & evidence

ORD record: ord-79ed68bc3c5e41dc9613b7081fe3174b
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592363B2

Reaction notes

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