Isopropylamine → N-((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)methyl)propan-2-amine

HRID 562178Notes

Reaction equation

HRID 562178 reaction equation
C1(C[NH:5][CH2:6][C:7]2[CH:8]=[N:9][CH:10]=[C:11]([B:13]3[O:17][C:16]([CH3:19])([CH3:18])[C:15]([CH3:21])([CH3:20])[O:14]3)[CH:12]=2)CC1.C(S(N1CC[CH:30](C2C3C(=C(C(N)=O)C=C(C4C=NC=C(CNC(C)C)C=4)C=3)NC=2)[CH2:29][CH2:28]1)(=O)=O)C.C(N)(C)C.CC1(C)C(C)(C)OB(C2C=C(C=O)C=NC=2)O1.[BH3-]C#N.[Na+]>CO>[CH3:28][CH:29]([NH:5][CH2:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([B:13]2[O:17][C:16]([CH3:18])([CH3:19])[C:15]([CH3:20])([CH3:21])[O:14]2)[CH:12]=1)[CH3:30]

Participants

7

Reactant 5

HCID 6363IsopropylamineHCID 49926405-(Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 574157101-cyclopropyl-N-((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)methyl)methanamineHCID 577327213-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-{[(1-methylethyl)amino]methyl}-3-pyridinyl)-1H-indole-7-carboxamide

Product 1

HCID 57415713N-((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)methyl)propan-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The (cyclopropylmethyl){[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl]methyl}amine used to prepare 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-{[(1-methylethyl)amino]methyl}-3-pyridinyl)-1H-indole-7-carboxamide was prepared as follows: isopropylamine (0.011 mL, 0.129 mmol) was added to a solution of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinecarbaldehyde (30 mg, 0.129 mmol) in MeOH (1 mL) in a 2-dram vial. NaCNBH3 (16 mg, 0.258 mmol) was then added, the vial was capped and the reaction was stirred at room temperature for 24 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 22 mg of crude (1-methylethyl){[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl]methyl}amine.

Workup

  1. customwas prepared
  2. customthe vial was capped
  3. filtrationThe reaction mixture was filtered through a 2 g SCX cartridge (pre-equilibrated with 3 mL MeOH)
  4. washeluting in sequence with MeOH (6 mL)
  5. concentrationThe NH3/MeOH fraction was concentrated under a stream of nitrogen

Sources & evidence

ORD record
ord-146b804dfbae4840adbb4d60e2f607a0
Source dataset
uspto-grants-2011_11
Patent number
US08063071B2

Reaction notes

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