Boron tribromide → HCID 24764714, compound

HRID 335103Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of N-(5-(3-methoxyphenylthio)-3-phenoxypyridin-2-yl)-4-methylthiazol-2-amine (prepared according to Example 56; 1.1 g, 2.6 mmol) and CH2Cl2 (20 mL) was cooled to 0° C. and tribromoborane (1M in CH2Cl2, 7.83 mL, 7.83 mmol) was added and stirred at 0° C. for 1 hour. The reaction was slowly poured into saturated aqueous sodium bicarbonate and extracted with 10% methanol in CH2Cl2. The organic layer was dried with sodium sulfate, filtered and concentrated. The residue was purified on silica gel (50 to 80% EtOAc in hexanes) to afford 3-(6-(4-methylthiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)phenol (692 mg, 65.1% yield) as a white solid. 1H NMR (d6-DMSO) δ 8.18 (dd, 1H), 7.37 (m, 2H), 7.31 (d, 1H), 7.19 (m, 1H), 7.16 (dd, 1H), 7.11-7.02 (m, 3H), 6.69-6.61 (m, 3H), 6.45 (m, 1H), 2.33 (s, 3H); Mass spectrum (esi) m/z=408.2 (M+H).

Workup

extractionextracted with 10% methanol in CH2Cl2
dry with materialThe organic layer was dried with sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified on silica gel (50 to 80% EtOAc in hexanes)

Sources & evidence

ORD record: ord-d581690059a2412c9a8db1d32448eadd
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883828B2

Reaction notes

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