1-bromo-3,3-dimethylpentan-2-one

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: The title compound was prepared from cyclopentylidene(6-methoxy-1H-indazol-3-yl)methyl dimethyl phosphate from Step B Example 6 and 1-Bromo-3,3-dimethylpentan-2-one from Step A Example 4 using the procedure described in Method I Step C of Example 1 followed by RP-HPLC purification using 35˜100% MeCN gradient without TFA. It was obtained as a colorless solid after lyophilization. LC-MS: 3.70 min. (m/Z=339.2, 465.2, 487.1). followed by RP-HPLC purification It was obtained as a colorless solid after lyophilization 3.70 min. (m/Z=339.2, 465.2, 487.1)

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

Procedure: The title compound was prepared from 1-(6-methoxy-1H-indazol-3-yl)-2-methylprop-1-en-1-yl dimethyl phosphate from Method I Step B of Example 1 and 1-bromo-3,3-dimethylpentan-2-one from the above using a procedure similar to described in Method I Step C of Example 1. It was purified on RP-HPLC using 30-100% MeCN gradient without TFA to give colorless solid after lyophilization. 1H NMR (CDCl3, 500 MHz) δ 7.70 (d, 9.0 Hz, 1H), 6.86 (dd, 2.1 & 8.9 Hz, 1H), 6.48 (d, 2.1 Hz, 1H), 5.29 (s, 2H), 3.86 (s, 3H), 3.56 (d, 11.3 Hz, 6H), 2.02 (d, 2.5 Hz, 3H), 1.82 (d, 3.5 Hz, 3H), 1.74 (q, 7.5 Hz, 2H), 1.28 (s, 6H), 0.94 (t, 7.6 Hz, 3H). NOE difference spectrum from irradiating 5.29 ppm singlet showed positive NOE at 6.48 ppm doublet and 1.28 ppm singlet. LC-MS: 3.48 min. (m/Z=313.2, 461.2, 439.2). It was purified on RP-HPLC to give colorless solid after lyophilization NOE difference spectrum from irradiating 5.29 ppm singlet 3.48 min. (m/Z=313.2, 461.2, 439.2)

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

Procedure: The title compound was prepared from cyclopentylidene(6-methoxy-1H-indazol-3-yl)methyl dimethyl phosphate from Step B Example 6 and 1-Bromo-3,3-dimethylpentan-2-one from Step A Example 4 using the procedure described in Method I Step C of Example 1 followed by RP-HPLC purification using 35˜100% MeCN gradient without TFA. It was obtained as a colorless solid after lyophilization. LC-MS: 3.70 min. (m/Z=339.2, 465.2, 487.1). followed by RP-HPLC purification It was obtained as a colorless solid after lyophilization 3.70 min. (m/Z=339.2, 465.2, 487.1)

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

Procedure: The title compound was prepared from 1-(6-methoxy-1H-indazol-3-yl)-2-methylprop-1-en-1-yl dimethyl phosphate from Method I Step B of Example 1 and 1-bromo-3,3-dimethylpentan-2-one from the above using a procedure similar to described in Method I Step C of Example 1. It was purified on RP-HPLC using 30-100% MeCN gradient without TFA to give colorless solid after lyophilization. 1H NMR (CDCl3, 500 MHz) δ 7.70 (d, 9.0 Hz, 1H), 6.86 (dd, 2.1 & 8.9 Hz, 1H), 6.48 (d, 2.1 Hz, 1H), 5.29 (s, 2H), 3.86 (s, 3H), 3.56 (d, 11.3 Hz, 6H), 2.02 (d, 2.5 Hz, 3H), 1.82 (d, 3.5 Hz, 3H), 1.74 (q, 7.5 Hz, 2H), 1.28 (s, 6H), 0.94 (t, 7.6 Hz, 3H). NOE difference spectrum from irradiating 5.29 ppm singlet showed positive NOE at 6.48 ppm doublet and 1.28 ppm singlet. LC-MS: 3.48 min. (m/Z=313.2, 461.2, 439.2). It was purified on RP-HPLC to give colorless solid after lyophilization NOE difference spectrum from irradiating 5.29 ppm singlet 3.48 min. (m/Z=313.2, 461.2, 439.2)

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: The title compound was prepared from cyclopentylidene(6-methoxy-1H-indazol-3-yl)methyl dimethyl phosphate from Step B Example 6 and 1-Bromo-3,3-dimethylpentan-2-one from Step A Example 4 using the procedure described in Method I Step C of Example 1 followed by RP-HPLC purification using 35˜100% MeCN gradient without TFA. It was obtained as a colorless solid after lyophilization. LC-MS: 3.70 min. (m/Z=339.2, 465.2, 487.1). followed by RP-HPLC purification It was obtained as a colorless solid after lyophilization 3.70 min. (m/Z=339.2, 465.2, 487.1)

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

Procedure: The title compound was prepared from 1-(6-methoxy-1H-indazol-3-yl)-2-methylprop-1-en-1-yl dimethyl phosphate from Method I Step B of Example 1 and 1-bromo-3,3-dimethylpentan-2-one from the above using a procedure similar to described in Method I Step C of Example 1. It was purified on RP-HPLC using 30-100% MeCN gradient without TFA to give colorless solid after lyophilization. 1H NMR (CDCl3, 500 MHz) δ 7.70 (d, 9.0 Hz, 1H), 6.86 (dd, 2.1 & 8.9 Hz, 1H), 6.48 (d, 2.1 Hz, 1H), 5.29 (s, 2H), 3.86 (s, 3H), 3.56 (d, 11.3 Hz, 6H), 2.02 (d, 2.5 Hz, 3H), 1.82 (d, 3.5 Hz, 3H), 1.74 (q, 7.5 Hz, 2H), 1.28 (s, 6H), 0.94 (t, 7.6 Hz, 3H). NOE difference spectrum from irradiating 5.29 ppm singlet showed positive NOE at 6.48 ppm doublet and 1.28 ppm singlet. LC-MS: 3.48 min. (m/Z=313.2, 461.2, 439.2). It was purified on RP-HPLC to give colorless solid after lyophilization NOE difference spectrum from irradiating 5.29 ppm singlet 3.48 min. (m/Z=313.2, 461.2, 439.2)