[2-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]phenyl]boronic acid

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

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

Procedure: 83 ml of 1,2-dimethoxyethane were aerated with argon, and 481 mg (0.41 mmol) of Pd(PPh3)4 and 1.9 g (8.3 mmol) of ethyl 6-bromopicolinate were added. After 10 min, 3.16 g (12.5 mmol) of 2-(tert-butoxycarbonylaminomethyl)phenylboronic acid and finally 8.3 ml of a 2M sodium carbonate solution were added. The mixture was heated to reflux under argon for 18 h, diluted with dichloromethane after cooling and washed with water. The organic phase was dried, concentrated and purified by chromatography on silica gel. 2.12 g (72%) of a viscous orange oil were obtained. were added The mixture was heated to reflux under argon for 18 h after cooling washed with water The organic phase was dried concentrated purified by chromatography on silica gel

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

Procedure: 150 ml of 1,2-dimethoxyethane were aerated with argon, and 874 mg (0.75 mmol) of Pd(PPh3)4 and 3.45 g (15 mmol) ethyl 3-bromopyridine-2-carboxylate were added. After 10 min, 5.53 g (22.5 mmol) of 2-(tert-butoxycarbonylaminomethyl)phenylboronic acid and finally 15 ml of a 2M sodium carbonate solution were added. The mixture was heated to reflux for 18 h under argon, diluted with dichloromethane after cooling and washed with water. The organic phase was dried, concentrated and purified by chromatography on silica gel. 3.4 g (66%) of a viscous oil were obtained. MS (ES+): m/z=357 (M+1). were added The mixture was heated to reflux for 18 h under argon after cooling washed with water The organic phase was dried concentrated purified by chromatography on silica gel

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

Procedure: 107 ml of 1,2-dimethoxyethane were aerated with argon, and 597 mg (0.51 mmol) of Pd(PPh3)4 and 2.24 g (10.3 mmol) of methyl 3-brompyrazine-2-carboxylate were added. After 10 min, 3.9 g (15.45 mmol) of 2-(tert-butoxycarbonylaminomethyl)-phenylboronic acid and finally 10.7 ml of a 2M sodium carbonate solution were added. The mixture was heated to reflux for 18 h under argon, diluted with dichloromethane after cooling and washed with water. The organic phase was dried, concentrated and purified by chromatography on silica gel. 661 mg (19%) of a viscous oil were obtained. MS (ES+): m/z=344 (M+1), 288 (M−55). 1H-NMR (CDCl3): δ=8.78 (1H, d, J=2.4 Hz), 8.67 (1H, d, J=2.4 Hz), 7.54-7.14 (4H, m), 5.11 (1H, br s), 4.22 (2H, d, J=5.9 Hz), 3.79 (3H, s), 1.38 (9H, s). were added The mixture was heated to reflux for 18 h under argon after cooling washed with water The organic phase was dried concentrated purified by chromatography on silica gel

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

Procedure: 107 ml of 1,2-dimethoxyethane were aerated with argon, and 597 mg (0.51 mmol) of Pd(PPh3)4 and 2.24 g (10.3 mmol) of methyl 3-brompyrazine-2-carboxylate were added. After 10 min, 3.9 g (15.45 mmol) of 2-(tert-butoxycarbonylaminomethyl)-phenylboronic acid and finally 10.7 ml of a 2M sodium carbonate solution were added. The mixture was heated to reflux for 18 h under argon, diluted with dichloromethane after cooling and washed with water. The organic phase was dried, concentrated and purified by chromatography on silica gel. 661 mg (19%) of a viscous oil were obtained. MS (ES+): m/z=344 (M+1), 288 (M−55). 1H-NMR (CDCl3): δ=8.78 (1H, d, J=2.4 Hz), 8.67 (1H, d, J=2.4 Hz), 7.54-7.14 (4H, m), 5.11 (1H, br s), 4.22 (2H, d, J=5.9 Hz), 3.79 (3H, s), 1.38 (9H, s). were added The mixture was heated to reflux for 18 h under argon after cooling washed with water The organic phase was dried concentrated purified by chromatography on silica gel

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

Procedure: 83 ml of 1,2-dimethoxyethane were aerated with argon, and 481 mg (0.41 mmol) of Pd(PPh3)4 and 1.9 g (8.3 mmol) of ethyl 6-bromopicolinate were added. After 10 min, 3.16 g (12.5 mmol) of 2-(tert-butoxycarbonylaminomethyl)phenylboronic acid and finally 8.3 ml of a 2M sodium carbonate solution were added. The mixture was heated to reflux under argon for 18 h, diluted with dichloromethane after cooling and washed with water. The organic phase was dried, concentrated and purified by chromatography on silica gel. 2.12 g (72%) of a viscous orange oil were obtained. were added The mixture was heated to reflux under argon for 18 h after cooling washed with water The organic phase was dried concentrated purified by chromatography on silica gel

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

Procedure: 150 ml of 1,2-dimethoxyethane were aerated with argon, and 874 mg (0.75 mmol) of Pd(PPh3)4 and 3.45 g (15 mmol) ethyl 3-bromopyridine-2-carboxylate were added. After 10 min, 5.53 g (22.5 mmol) of 2-(tert-butoxycarbonylaminomethyl)phenylboronic acid and finally 15 ml of a 2M sodium carbonate solution were added. The mixture was heated to reflux for 18 h under argon, diluted with dichloromethane after cooling and washed with water. The organic phase was dried, concentrated and purified by chromatography on silica gel. 3.4 g (66%) of a viscous oil were obtained. MS (ES+): m/z=357 (M+1). were added The mixture was heated to reflux for 18 h under argon after cooling washed with water The organic phase was dried concentrated purified by chromatography on silica gel

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

Procedure: 107 ml of 1,2-dimethoxyethane were aerated with argon, and 597 mg (0.51 mmol) of Pd(PPh3)4 and 2.24 g (10.3 mmol) of methyl 3-brompyrazine-2-carboxylate were added. After 10 min, 3.9 g (15.45 mmol) of 2-(tert-butoxycarbonylaminomethyl)-phenylboronic acid and finally 10.7 ml of a 2M sodium carbonate solution were added. The mixture was heated to reflux for 18 h under argon, diluted with dichloromethane after cooling and washed with water. The organic phase was dried, concentrated and purified by chromatography on silica gel. 661 mg (19%) of a viscous oil were obtained. MS (ES+): m/z=344 (M+1), 288 (M−55). 1H-NMR (CDCl3): δ=8.78 (1H, d, J=2.4 Hz), 8.67 (1H, d, J=2.4 Hz), 7.54-7.14 (4H, m), 5.11 (1H, br s), 4.22 (2H, d, J=5.9 Hz), 3.79 (3H, s), 1.38 (9H, s). were added The mixture was heated to reflux for 18 h under argon after cooling washed with water The organic phase was dried concentrated purified by chromatography on silica gel

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

Procedure: 83 ml of 1,2-dimethoxyethane were aerated with argon, and 481 mg (0.41 mmol) of Pd(PPh3)4 and 1.9 g (8.3 mmol) of ethyl 6-bromopicolinate were added. After 10 min, 3.16 g (12.5 mmol) of 2-(tert-butoxycarbonylaminomethyl)phenylboronic acid and finally 8.3 ml of a 2M sodium carbonate solution were added. The mixture was heated to reflux under argon for 18 h, diluted with dichloromethane after cooling and washed with water. The organic phase was dried, concentrated and purified by chromatography on silica gel. 2.12 g (72%) of a viscous orange oil were obtained. were added The mixture was heated to reflux under argon for 18 h after cooling washed with water The organic phase was dried concentrated purified by chromatography on silica gel