Ethyl Acetate → HCID 68679989, compound

HRID 1869349Notes

Reaction equation

[F:1][C:2]([F:30])([F:29])[C:3]([CH:18]=[N:19][C:20]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:21]=1[CH:22]=[N:23][NH:24]2)([OH:17])[CH2:4][C:5]([C:8]1[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][C:9]=1[O:15][CH3:16])([CH3:7])[CH3:6].B(Br)(Br)Br.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>ClCCl>[Br:14][C:12]1[CH:11]=[CH:10][C:9]([O:15][CH3:16])=[C:8]2[C:13]=1[CH:18]([NH:19][C:20]1[CH:28]=[CH:27][CH:26]=[C:25]3[C:21]=1[CH:22]=[N:23][NH:24]3)[C:3]([C:2]([F:29])([F:1])[F:30])([OH:17])[CH2:4][C:5]2([CH3:7])[CH3:6]

Participants

Conditions

Temperature: -30 °C

Procedure

100 mg (0.206 mmol) of 1,1,1-trifluoro-4-(5-bromo-2-methoxyphenyl)-2-[(1H-indazol-4-yl)iminomethyl]-4-methylpentan-2-ol is dissolved in one milliliter of dichloromethane, and the reaction mixture is cooled to −30° C. Four milliliters of a 1 M solution of BBr3 in dichloromethane is added in drops within 15 minutes, and the batch is then stirred for 45 more minutes at −30° C. At −30° C., about 10 ml of a saturated sodium bicarbonate solution is carefully added in drops. After dilution with ethyl acetate, it is stirred for ten minutes and then extracted twice with 50 ml each of ethyl acetate. The combined organic extracts are washed with water and brine. The residue that is obtained after the solvent is dried and spun off is chromatographed several times on silica gel (mobile solvent ethyl acetate/dichloromethane). 21 mg of the desired compound (together with the corresponding Desbrom compound) is isolated.

Workup

extractionextracted twice with 50 ml each of ethyl acetate
washThe combined organic extracts are washed with water and brine
customThe residue that is obtained after the solvent
customis dried
customis chromatographed several times on silica gel (mobile solvent ethyl acetate/dichloromethane)

Sources & evidence

ORD record: ord-7a552734060e4d66b4805cde074b3d4b
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07638515B2

Reaction notes

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