4-Benzothiazolol

4-Hydroxy-benzothiazole Boron bromide (3. 09ML, 1M solution in DCM, 3.09 mmol) was added dropwise at 0 C to a stirred solution OF 4-METHOXY-BENZOTHIAZOLE (510 mg, 3.09 mmol) in dry DCM (30ML). The resulting solution was warmed to 40 C and allowed to stir overnight. The resulting solution was concentrated IIZ vacuo and diluted with water and HCl (2N). The aqueous phase was neutralised to pH-7 with NaHC03 and the solution extracted with EtOAc (3 x 100 ml) and the combined organic extracts dried (MGS04) and the solvent removed III vacuo. The resulting oil was purified by flash chromatography eluting silica gel with hexane: EtOAc [4: 1] to hexane: EtOAc [7: 3] to give the title compound as a tan solid (730mg, 80percent) ; ON (300 MHz, CDC13) 7.59 (1H, s, C$, 7.46 (1H, dd, Ar), 7.36 (1H, t, Ar), 7.02 (1H, dd, Ar).b) 4-Hydroxy-benzothiazole Boron tribromide (3. 09m1, 1M solution in DCM, 3.09 mmol) was added dropwise at 0 C to a stirred solution of 4-methoxy-benzothiazole (510 mg, 3.09 mmol) in dry DCM (30MOL). The resulting solution was warmed to 40 C and allowed to stir overnight. The resulting solution was concentrated in vacuo and diluted with water and HCl (2N). The aqueous phase was neutralised to PH-7 with NAHCO3 and the solution extracted with EtOAc (3 x 100 ml) and the combined organic extracts dried (MGS04) and the solvent removed in vacuo. The resulting oil was purified by flash chromatography eluting silica gel with hexane: EtOAc [4 : 1] to hexane: EtOAc [7: 3] to give the title compound as a tan solid (730mg, 80percent) ; BH (300 MHz, CDCL3) 7.59 (1H, s, CH), 7. 46 (1H, dd, Ar), 7.36 (1H, t, Ar), 7.02 (1H, dd, Ar).Boron tribromide (3. 09ML, 1M solution in DCM, 3.09 mmol) was added dropwise at 0 °C to a stirred solution of 4-methoxy-benzothiazole (510 mg, 3.09 mmol) in dry DCM (30ML). The resulting solution was warmed to 40 °C and allowed to stir overnight. The resulting solution was concentrated in vacuo and diluted with water and HCl (2N). The aqueous phase was neutralised to pH-7 with NAHCO3 and the solution extracted with EtOAc (3 x 100 ml) and the combined organic extracts dried (MGS04) and the solvent removed in vacuo. The resulting oil was purified by flash chromatography eluting silica gel with hexane: EtOAc [4: 1] to hexane: EtOAc [7: 3] to give the title compound as a tan solid (730mg, 80percent) ; ON (300 MHz, CDC13) 7.59 (1H, s, CH), 7.46 (1H, dd, Ar), 7.36 (1H, t, Ar), 7.02 (1H, dd, Ar)To a stirred solution of terf-butyl 3-((methylsulfonyl)oxy)azetidine-1 -carboxylate (Intermediate 1) (1 .47 g, 5.85 mmol) and To a stirred solution of tert-butyl 2-methyl-3-((methylsulfonyl)oxy)azetidine-1- carboxylate (Intermediate 99A) (184 mg, 0.693 mmol) and To a stirred solution of tert-butyl 2-methyl-3-((methylsulfonyl)oxy)azetidine-1 - carboxylate (Intermediate 99A) (1 .40 g, 5.28 mmol) and Triphenylphosphine (9.72 g, 37.0 mmol) was added to a solution of benzo[d]thiazol-4- ol (4.00 g, 26.5 mmol) in tetrahydrofuran (80 ml_). The reaction mixture was cooled to 0 °C, and (c/s)-methyl 3-hydroxycyclobutanecarboxylate (4.13 g, 31 .7 mmol) was added, followed by the dropwise addition of DIAD (7.20 ml_, 37.0 mmol). The reaction mixture was then warmed to room temperature, stirred over the weekend, and concentrated. The remaining material was purified on silica gel eluting with a 15percent-60percent EtOAc-hexanes gradient. The appropriate fractions were combined, evaporated under reduced pressure and placed in vacuo to give the title compound (6.72 g, 90percent) which contained about 1 .1 equivalent of reduced DIAD contaminant. 1H NMR (400 MHz, CD3SOCD3) delta 2.51 -2.67 (m, 2 H), 2.75 (td, J = 7, 4 Hz, 2H), 3.10-3.19 (m, 1 H), 3.67 (s, 3 H), 5.03-5.10 (m, 1 H), 6.68 (d, J = 8 Hz, 1 H), 7.26 (t, J = 8 Hz, 1 H), 7.45 (d, J = 8 Hz, 1 H), 8.84 (s, 1 H); LC-MS (LC-ES) M+H = 264.

Molecular Weight:151.19
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:151.00918496
Monoisotopic Mass:151.00918496
Topological Polar Surface Area:61.4
Heavy Atom Count:10
Complexity:131
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes