Sodium Bicarbonate → 1-[(1H-Indazol-4-yl)amino]-4,4-dimethyl-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-2-ol

HRID 1869353Notes

Reaction equation

[F:1][C:2]([F:27])([F:26])[C:3]([CH:15]=[N:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:18]=1[CH:19]=[N:20][NH:21]2)([OH:14])[CH2:4][C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:7])[CH3:6].C(=O)(O)[O-].[Na+]>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[NH:21]1[C:22]2[C:18](=[C:17]([NH:16][CH:15]3[C:9]4[C:8](=[CH:13][CH:12]=[CH:11][CH:10]=4)[C:5]([CH3:7])([CH3:6])[CH2:4][C:3]3([C:2]([F:1])([F:26])[F:27])[OH:14])[CH:25]=[CH:24][CH:23]=2)[CH:19]=[N:20]1

Participants

Conditions

Temperature: -70 °C

Procedure

190 mg (0.51 mmol) of 1,1,1-trifluoro-4-phenyl-2-[(1H-indazol-4-yl)iminomethyl]-4-methylpentan-2-ol is dissolved in 100 ml of dichloromethane and cooled to −70° C. The solution is mixed over 10 minutes with 9 ml of titanium tetrachloride solution (1 mol in dichloromethane), and it is stirred for 1 hour at −70° C. Then, the cold solution is poured into 200 ml of saturated sodium bicarbonate solution and stirred for 15 minutes. For working-up, the mixture is extracted with dichloromethane, the organic phase is washed with saturated sodium chloride solution, dried with sodium sulfate and concentrated by evaporation in a vacuum: 208 mg. Column chromatography with dichloromethane-methanol yields 53 mg (28%) of the desired product.

Workup

stirringstirred for 15 minutes
extractionthe mixture is extracted with dichloromethane
washthe organic phase is washed with saturated sodium chloride solution
dry with materialdried with sodium sulfate
concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record: ord-a1c5bc79bf164a2cb7b0d79588a23cfb
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07638515B2

Reaction notes

Loading…