isocyanoimino(triphenyl)-lambda5-phosphane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of N-isocyaniminotriphenylphosphorane (0.204 g, 0.678 mmol), 3,4-dichlorobenzaldhyde (0.158 g, 2.712 mmol), and 2-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)acetic acid (0.150 g, 0.678 mmol) in dichloromethane (5 mL) was stirred at room temperature overnight. Solvent was removed under vacuum. The crude product was recystallised in ACN/Ethanol to afford 6-((5-((3,4-dichlorophenyl)(hydroxy)methyl)-1,3,4-oxadiazol-2-yl)methoxy)-3,4-dihydroquinolin-2(1H)-one (40 mg, 14%) as an off white solid. 1H NMR: 400 MHZ, DMSO-d6: δ 2.40 (t, J=7.20 Hz, 2H), 2.82 (t, J=8.00 Hz, 2H), 5.32 (s, 2H), 6.11 (d, J=5.60 Hz, 1H), 6.77 (d, J=8.40 Hz, 1H), 6.82 (dd, J=2.40, 8.60 Hz, 1H), 6.88 (s, 1H), 7.00 (d, J=5.60 Hz, 1H), 7.45 (dd, J=1.60, 8.40 Hz, 1H), 7.67 (d, J=8.40 Hz, 1H), 7.72 (d, J=1.60 Hz, 1H), 9.95 (s, 1H). LCMS: RT 1.76 min. LCMS (ES-API), m/z 422.0 (M+H). Solvent was removed under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of N-isocyaniminotriphenylphosphorane (0.204 g, 0.678 mmol), 3,4-dichlorobenzaldhyde (0.158 g, 2.712 mmol), and 2-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)acetic acid (0.150 g, 0.678 mmol) in dichloromethane (5 mL) was stirred at room temperature overnight. Solvent was removed under vacuum. The crude product was recystallised in ACN/Ethanol to afford 6-((5-((3,4-dichlorophenyl)(hydroxy)methyl)-1,3,4-oxadiazol-2-yl)methoxy)-3,4-dihydroquinolin-2(1H)-one (40 mg, 14%) as an off white solid. 1H NMR: 400 MHZ, DMSO-d6: δ 2.40 (t, J=7.20 Hz, 2H), 2.82 (t, J=8.00 Hz, 2H), 5.32 (s, 2H), 6.11 (d, J=5.60 Hz, 1H), 6.77 (d, J=8.40 Hz, 1H), 6.82 (dd, J=2.40, 8.60 Hz, 1H), 6.88 (s, 1H), 7.00 (d, J=5.60 Hz, 1H), 7.45 (dd, J=1.60, 8.40 Hz, 1H), 7.67 (d, J=8.40 Hz, 1H), 7.72 (d, J=1.60 Hz, 1H), 9.95 (s, 1H). LCMS: RT 1.76 min. LCMS (ES-API), m/z 422.0 (M+H). Solvent was removed under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (22.2 g, 68.1 mmol) in THF (360 mL) was added (isocyanoimino)triphenylphosphorane (20.6 g, 68.1 mmol) portionwise over 1 hour. The resultant mixture was stirred at RT for 18 hours before being concentrated in vacuo and triturated with 1:1 DCM/cyclohexane (200 mL). The title compound was collected by filtration as a yellow solid (14.5 g, 61%). LCMS: RT=4.03 min, M+H+=350/352. before being concentrated in vacuo triturated with 1:1 DCM/cyclohexane (200 mL) The title compound was collected by filtration as a yellow solid (14.5 g, 61%)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (22.2 g, 68.1 mmol) in THF (360 mL) was added (isocyanoimino)triphenylphosphorane (20.6 g, 68.1 mmol) portionwise over 1 hour. The resultant mixture was stirred at RT for 18 hours before being concentrated in vacuo and triturated with 1:1 DCM/cyclohexane (200 mL). The title compound was collected by filtration as a yellow solid (14.5 g, 61%). LCMS: RT=4.03 min, M+H+=350/352. before being concentrated in vacuo triturated with 1:1 DCM/cyclohexane (200 mL) The title compound was collected by filtration as a yellow solid (14.5 g, 61%)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (isocyanoimino)triphenylphosphorane (978 mg, 3.24 mmol) in anhydrous CH2Cl2 (30 mL) was added dropwise a solution of 3-(2-(naphthalen-1-yl)acetamido)thiophene-2-carboxylic acid (340 mg, 1.09 mmol) in anhydrous CH2Cl2 (27 mL). The resulting mixture was stirred at room temperature under nitrogen overnight and evaporated under reduced pressure. Purification by flash chromatography (silica, 30:70 ethyl acetate/hexane) gave N-(2-(1,3,4-oxadiazol-2-yl)thiophen-3-yl)-2-(naphthalen-1-yl)acetamide (45 mg, 12%). Method [7] m/z 357.9 (M+Na); retention time=5.919. 1H-NMR (CDCl3) δ 8.18 (d, J=1.1 Hz, 1H), 8.16 (d, J=1.4 Hz, 1H), 8.05 (d, J=8.3 Hz, 1H), 7.88 (d, J=8.0 Hz, 2H), 7.61-7.41 (m, 5H), 4.27 (s, 2H). evaporated under reduced pressure Purification by flash chromatography (silica, 30:70 ethyl acetate/hexane)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (22.2 g, 68.1 mmol) in THF (360 mL) was added (isocyanoimino)triphenylphosphorane (20.6 g, 68.1 mmol) portionwise over 1 hour. The resultant mixture was stirred at RT for 18 hours before being concentrated in vacuo and triturated with 1:1 DCM/cyclohexane (200 mL). The title compound was collected by filtration as a yellow solid (14.5 g, 61%). LCMS: RT=4.03 min, M+H+=350/352. before being concentrated in vacuo triturated with 1:1 DCM/cyclohexane (200 mL) The title compound was collected by filtration as a yellow solid (14.5 g, 61%)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (isocyanoimino)triphenylphosphorane (978 mg, 3.24 mmol) in anhydrous CH2Cl2 (30 mL) was added dropwise a solution of 3-(2-(naphthalen-1-yl)acetamido)thiophene-2-carboxylic acid (340 mg, 1.09 mmol) in anhydrous CH2Cl2 (27 mL). The resulting mixture was stirred at room temperature under nitrogen overnight and evaporated under reduced pressure. Purification by flash chromatography (silica, 30:70 ethyl acetate/hexane) gave N-(2-(1,3,4-oxadiazol-2-yl)thiophen-3-yl)-2-(naphthalen-1-yl)acetamide (45 mg, 12%). Method [7] m/z 357.9 (M+Na); retention time=5.919. 1H-NMR (CDCl3) δ 8.18 (d, J=1.1 Hz, 1H), 8.16 (d, J=1.4 Hz, 1H), 8.05 (d, J=8.3 Hz, 1H), 7.88 (d, J=8.0 Hz, 2H), 7.61-7.41 (m, 5H), 4.27 (s, 2H). evaporated under reduced pressure Purification by flash chromatography (silica, 30:70 ethyl acetate/hexane)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (22.2 g, 68.1 mmol) in THF (360 mL) was added (isocyanoimino)triphenylphosphorane (20.6 g, 68.1 mmol) portionwise over 1 hour. The resultant mixture was stirred at RT for 18 hours before being concentrated in vacuo and triturated with 1:1 DCM/cyclohexane (200 mL). The title compound was collected by filtration as a yellow solid (14.5 g, 61%). LCMS: RT=4.03 min, M+H+=350/352. before being concentrated in vacuo triturated with 1:1 DCM/cyclohexane (200 mL) The title compound was collected by filtration as a yellow solid (14.5 g, 61%)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of N-isocyaniminotriphenylphosphorane (0.204 g, 0.678 mmol), 3,4-dichlorobenzaldhyde (0.158 g, 2.712 mmol), and 2-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)acetic acid (0.150 g, 0.678 mmol) in dichloromethane (5 mL) was stirred at room temperature overnight. Solvent was removed under vacuum. The crude product was recystallised in ACN/Ethanol to afford 6-((5-((3,4-dichlorophenyl)(hydroxy)methyl)-1,3,4-oxadiazol-2-yl)methoxy)-3,4-dihydroquinolin-2(1H)-one (40 mg, 14%) as an off white solid. 1H NMR: 400 MHZ, DMSO-d6: δ 2.40 (t, J=7.20 Hz, 2H), 2.82 (t, J=8.00 Hz, 2H), 5.32 (s, 2H), 6.11 (d, J=5.60 Hz, 1H), 6.77 (d, J=8.40 Hz, 1H), 6.82 (dd, J=2.40, 8.60 Hz, 1H), 6.88 (s, 1H), 7.00 (d, J=5.60 Hz, 1H), 7.45 (dd, J=1.60, 8.40 Hz, 1H), 7.67 (d, J=8.40 Hz, 1H), 7.72 (d, J=1.60 Hz, 1H), 9.95 (s, 1H). LCMS: RT 1.76 min. LCMS (ES-API), m/z 422.0 (M+H). Solvent was removed under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (22.2 g, 68.1 mmol) in THF (360 mL) was added (isocyanoimino)triphenylphosphorane (20.6 g, 68.1 mmol) portionwise over 1 hour. The resultant mixture was stirred at RT for 18 hours before being concentrated in vacuo and triturated with 1:1 DCM/cyclohexane (200 mL). The title compound was collected by filtration as a yellow solid (14.5 g, 61%). LCMS: RT=4.03 min, M+H+=350/352. before being concentrated in vacuo triturated with 1:1 DCM/cyclohexane (200 mL) The title compound was collected by filtration as a yellow solid (14.5 g, 61%)