Reaction equation
C(NCC1SC([B:10]([OH:12])[OH:11])=CC=1)C.[CH2:13]([CH:15]([CH2:47][CH3:48])[CH2:16][NH:17][CH2:18][C:19]1[S:23][C:22](C2C=C3C(=C(C(N)=O)C=2)NC=C3C2CCN(S(CC)(=O)=O)CC2)=[CH:21][CH:20]=1)[CH3:14].C(C1SC(B(O)O)=CC=1)=O.[BH3-]C#N.[Na+].C(C(CC)CN)C>CO>[CH2:13]([CH:15]([CH2:47][CH3:48])[CH2:16][NH:17][CH2:18][C:19]1[S:23][C:22]([B:10]([OH:12])[OH:11])=[CH:21][CH:20]=1)[CH3:14]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
The {5-[(ethylamino)methyl]-2-thienyl}boronic acid used to prepare 5-(5-{[(2-ethylbutyl)amino]methyl}-2-thienyl)-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide was prepared as follows: A solution of (5-formyl-2-thienyl)boronic acid (50 mg, 0.32 mmol) in MeOH (0.5 mL) and a solution of NaCNBH3 (40 mg, 0.64 mmol) in MeOH (0.5 mL) were added to (2-ethylbutyl)amine (32 mg, 0.32 mmol) in a 2-dram vial. The vial was capped and the reaction was stirred at room temperature for 20 h. The reaction mixture was filtered through a 2 g SCX cartridge (pre-equilibrated with 3 mL MeOH), eluting in sequence with MeOH (6 mL) and a 2 M solution of NH3/MeOH (9 mL). The NH3/MeOH fraction was concentrated under a stream of nitrogen to give 48 mg of crude (5-{[(2-ethylbutyl)amino]methyl}-2-thienyl)boronic acid.
Workup
- customwas prepared
- customThe vial was capped
- filtrationThe reaction mixture was filtered through a 2 g SCX cartridge (pre-equilibrated with 3 mL MeOH)
- washeluting in sequence with MeOH (6 mL)
- concentrationThe NH3/MeOH fraction was concentrated under a stream of nitrogen
Sources & evidence
- ORD record
- ord-3287b9f646194fe3b858a566e34177aa
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063071B2
Linked notes
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