4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine → N2-[(3,4-Dimethoxyphenyl)methyl]-6-(trifluoromethyl)[4,4′-bipyridine]-2,3′-diamine

HRID 69955Notes

Reaction equation

HRID 69955 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH2:6][NH:7][C:8]1[CH:13]=[C:12](I)[CH:11]=[C:10]([C:15]([F:18])([F:17])[F:16])[N:9]=1.CC1(C)C(C)(C)OB([C:32]2[CH:37]=[CH:36][N:35]=[CH:34][C:33]=2[NH2:38])O1>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH2:6][NH:7][C:8]1[CH:13]=[C:12]([C:32]2[CH:37]=[CH:36][N:35]=[CH:34][C:33]=2[NH2:38])[CH:11]=[C:10]([C:15]([F:18])([F:17])[F:16])[N:9]=1

Participants

5

Reactant 2

HCID 497604144-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amineHCID 69047366N-(3,4-dimethoxybenzyl)-4-iodo-6-(trifluoromethyl)pyridin-2-amine

Product 1

HCID 68161531N2-[(3,4-Dimethoxyphenyl)methyl]-6-(trifluoromethyl)[4,4′-bipyridine]-2,3′-diamineYield 38%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Method 26 was followed using N-(3,4-dimethoxybenzyl)-4-iodo-6-(tri-fluoromethyl)pyridin-2-amine (1.0 equiv.), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine (3 equiv.), Pd(dppf)Cl2 DCM (0.10 equiv.) in DME/2M Na2CO3 (3:1, 0.07 M) at 50° C. for 45 min. Purification via reverse phase HPLC afforded N2-(3,4-dimethoxybenzyl)-6-(trifluoromethyl)-4,4′-bipyridine-2,3′-diamine in 38% yield. LCMS (m/z): 402.1 (MH+); LC Rt=3.0 min.

Workup

  1. customat 50° C.
  2. customfor 45 min
  3. customPurification via reverse phase HPLC

Sources & evidence

ORD record
ord-91938574c3d44959a778d2be9cb33081
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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