Hydrochloric Acid → 5-(Benzyloxy)-2-methylbenzo[d]thiazol-7-ol
Reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11](Br)[C:12]2[S:16][C:15]([CH3:17])=[N:14][C:13]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.[OH-:50].[K+].Cl>O1CCOCC1.CCOC(C)=O.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([OH:50])[C:12]2[S:16][C:15]([CH3:17])=[N:14][C:13]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 90 °C
Procedure
5-(benzyloxy)-7-bromo-2-methylbenzo[d]thiazole 4.03D (560 mg, 1.7 mmol) Pd2(dba)3 (77 mg, 0.084 mmol), and 2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (142 mg, 0.335 mmol) were taken up in 1,4-dioxane (6 mL) under Ar. Aqueous 2 M KOH (2.5 mL, 5 mmol) was added and the mixture was heated to 90° C. After 1 h, the mixture was cooled to r.t. and was diluted with EtOAc (50 mL), and water (30 mL). The aqueous phase was and acidified with 3 M aqueous HCl (1.8 mL, 5.4 mmol). The phases were separated, and the organic phase was washed with saturated aqueous NaHCO3 (30 mL). The organic phase was dried over Na2SO4, filtered, and concentrated to afford a crude residue that was purified by silica gel chromatography (10-55% EtOAc in hexanes) to provide 5-(benzyloxy)-2-methylbenzo[d]thiazol-7-ol 4.03E. LCMS-ESI+ (m/z): [M+H]+ calcd for C15H14NO2S: 272.1; found 272.1.
Workup
- temperaturethe mixture was cooled to r.t.
- customThe phases were separated
- washthe organic phase was washed with saturated aqueous NaHCO3 (30 mL)
- dry with materialThe organic phase was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customto afford a crude residue that
- customwas purified by silica gel chromatography (10-55% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-54c4d8e89c0e4275b525f0c95c12e752
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376441B2
Reaction notes
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