1-(4-bromophenyl)-N-methylmethanamine

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

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

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

Procedure: A solution of triethylamine (0.22 ml, 1.6 mmol) in dichloromethane (10 ml) was treated with acetyl chloride (0.08 ml, 1.10 mmol), followed by 4-bromo-N-methylbenzylamine (210 mg, 1.05 mmol). This mixture was then stirred under an atmosphere of argon for 10 minutes. The reaction mixture was washed twice with water and the organic layer was separated and dried over sodium sulphate, and the solvent removed via rotary evaporation to give a yellow oil which was purified on a 5 g sep-pak column eluting from 0-100% ethyl acetate in petroleum ether to give the title compound as a yellow oil. The reaction mixture was washed twice with water the organic layer was separated dried over sodium sulphate the solvent removed via rotary evaporation to give a yellow oil which was purified on a 5 g sep-pak column eluting from 0-100% ethyl acetate in petroleum ether

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

Procedure: A solution of triethylamine (0.22 ml, 1.6 mmol) in dichloromethane (10 ml) was treated with acetyl chloride (0.08 ml, 1.10 mmol), followed by 4-bromo-N-methylbenzylamine (210 mg, 1.05 mmol). This mixture was then stirred under an atmosphere of argon for 10 minutes. The reaction mixture was washed twice with water and the organic layer was separated and dried over sodium sulphate, and the solvent removed via rotary evaporation to give a yellow oil which was purified on a 5 g sep-pak column eluting from 0-100% ethyl acetate in petroleum ether to give the title compound as a yellow oil. The reaction mixture was washed twice with water the organic layer was separated dried over sodium sulphate the solvent removed via rotary evaporation to give a yellow oil which was purified on a 5 g sep-pak column eluting from 0-100% ethyl acetate in petroleum ether

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

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

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

Procedure: 800 ml of an 8% solution of methylamine in toluene are added, whilst cooling with ice, to 100 g of 4-bromobenzaldehyde and 300 g of molecular sieve (3 Angstroms). The mixture is stirred overnight at ambient temperature, suction filtered to remove the molecular sieve and the solvent is evaporated off. The residue is dissolved in 1.4 litres of ice cold methanol and 48 g of sodium borohydride are added in batches whilst cooling with ice. Then the mixture is stirred for 30 minutes at 0° C., for one hour at 10° C. and for two hours at ambient temperature, then evaporated to dryness, the residue is taken up in ice water, acidified with half concentrated hydrochloric acid and extracted twice with ether. The ether is discarded, the aqueous phase is made alkaline with concentrated sodium hydroxide solution whilst cooling and then extracted three times with ether. The organic phase is washed with water and saturated saline solution, dried and evaporated down. 96.8 g of N-methyl-4-bromobenzylamine are obtained in the form of a colourless oil. suction filtered to remove the molecular sieve the solvent is evaporated off The residue is dissolved in 1.4 litres of ice cold methanol 48 g of sodium borohydride are added in batches whilst cooling with ice Then the mixture is stirred for 30 minutes at 0° C., for one hour at 10° C. and for two hours at ambient temperature evaporated to dryness extracted twice with ether whilst cooling extracted three times with ether The organic phase is washed with water and saturated saline solution dried evaporated down

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

Procedure: 800 ml of an 8% solution of methylamine in toluene are added, whilst cooling with ice, to 100 g of 4-bromobenzaldehyde and 300 g of molecular sieve (3 Angstroms). The mixture is stirred overnight at ambient temperature, suction filtered to remove the molecular sieve and the solvent is evaporated off. The residue is dissolved in 1.4 litres of ice cold methanol and 48 g of sodium borohydride are added in batches whilst cooling with ice. Then the mixture is stirred for 30 minutes at 0° C., for one hour at 10° C. and for two hours at ambient temperature, then evaporated to dryness, the residue is taken up in ice water, acidified with half concentrated hydrochloric acid and extracted twice with ether. The ether is discarded, the aqueous phase is made alkaline with concentrated sodium hydroxide solution whilst cooling and then extracted three times with ether. The organic phase is washed with water and saturated saline solution, dried and evaporated down. 96.8 g of N-methyl-4-bromobenzylamine are obtained in the form of a colourless oil. suction filtered to remove the molecular sieve the solvent is evaporated off The residue is dissolved in 1.4 litres of ice cold methanol 48 g of sodium borohydride are added in batches whilst cooling with ice Then the mixture is stirred for 30 minutes at 0° C., for one hour at 10° C. and for two hours at ambient temperature evaporated to dryness extracted twice with ether whilst cooling extracted three times with ether The organic phase is washed with water and saturated saline solution dried evaporated down

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

Procedure: 800 ml of an 8% solution of methylamine in toluene are added, whilst cooling with ice, to 100 g of 4-bromobenzaldehyde and 300 g of molecular sieve (3 Angstroms). The mixture is stirred overnight at ambient temperature, suction filtered to remove the molecular sieve and the solvent is evaporated off. The residue is dissolved in 1.4 litres of ice cold methanol and 48 g of sodium borohydride are added in batches whilst cooling with ice. Then the mixture is stirred for 30 minutes at 0° C., for one hour at 10° C. and for two hours at ambient temperature, then evaporated to dryness, the residue is taken up in ice water, acidified with half concentrated hydrochloric acid and extracted twice with ether. The ether is discarded, the aqueous phase is made alkaline with concentrated sodium hydroxide solution whilst cooling and then extracted three times with ether. The organic phase is washed with water and saturated saline solution, dried and evaporated down. 96.8 g of N-methyl-4-bromobenzylamine are obtained in the form of a colourless oil. suction filtered to remove the molecular sieve the solvent is evaporated off The residue is dissolved in 1.4 litres of ice cold methanol 48 g of sodium borohydride are added in batches whilst cooling with ice Then the mixture is stirred for 30 minutes at 0° C., for one hour at 10° C. and for two hours at ambient temperature evaporated to dryness extracted twice with ether whilst cooling extracted three times with ether The organic phase is washed with water and saturated saline solution dried evaporated down

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

Procedure: A solution of triethylamine (0.22 ml, 1.6 mmol) in dichloromethane (10 ml) was treated with acetyl chloride (0.08 ml, 1.10 mmol), followed by 4-bromo-N-methylbenzylamine (210 mg, 1.05 mmol). This mixture was then stirred under an atmosphere of argon for 10 minutes. The reaction mixture was washed twice with water and the organic layer was separated and dried over sodium sulphate, and the solvent removed via rotary evaporation to give a yellow oil which was purified on a 5 g sep-pak column eluting from 0-100% ethyl acetate in petroleum ether to give the title compound as a yellow oil. The reaction mixture was washed twice with water the organic layer was separated dried over sodium sulphate the solvent removed via rotary evaporation to give a yellow oil which was purified on a 5 g sep-pak column eluting from 0-100% ethyl acetate in petroleum ether

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

Procedure: Following the procedure outlined for Example 488, 1-bromo-4-(bromomethyl)benzene (1.0 g, 4.0 mmol) was reacted with methanamine (620 mg, 20 mmol) to afford the desired product (750 mg, 93%) as a brown solid: ESI MS m/z 201 [C8H10BrN+H]+.

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

Procedure: Following General Procedure E, 1-(4-bromophenyl)-N-methylmethanamine (200 mg, 1.0 mmol) was reacted to bis(pinacoato)diboron (280 mg, 1.1 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (310 mg, 1.0 mmol) to afford the desired product (145 mg, 42%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.65 (d, J=8.1 Hz, 2H), 7.58-7.52 (m, 2H), 7.42-7.35 (m, 3H), 6.02 (d, J=5.4 Hz, 1H), 4.33 (s, 2H), 3.73 (s, 3H), 2.83 (s, 3H). to afford the crude boronic ester which