Diisopropylethylamine → 3-{[Bis-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-pyridine-2-carbonitrile

HRID 251250Notes

Reaction equation

HRID 251250 reaction equation
[CH3:1][C:2]1[C:3]([CH2:8][NH:9][CH2:10][C:11]2[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][N:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[C:18]([C:20]1[C:25]([CH2:26]Br)=[CH:24][CH:23]=[CH:22][N:21]=1)#[N:19].CCN(C(C)C)C(C)C>CC#N>[CH3:1][C:2]1[C:3]([CH2:8][N:9]([CH2:26][C:25]2[C:20]([C:18]#[N:19])=[N:21][CH:22]=[CH:23][CH:24]=2)[CH2:10][C:11]2[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][N:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 103754503-(Bromomethyl)pyridine-2-carbonitrileHCID 45098010Bis-(3-methyl-pyridin-2-ylmethyl)-amine

Product 1

HCID 672723043-{[Bis-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-pyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using General Procedure A: Reaction of bis-(3-methyl-pyridin-2-ylmethyl)-amine in CH3CN with 2-cyano-3-bromomethyl-pyridine, KI and DIPEA gave 3-{[bis-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-pyridine-2-carbonitrile as a dark red oil. 1H NMR (CDCl3) δ 2.04 (s, 6H), 3.86 (s, 4H), 3.99 (s, 2H), 7.07 (m, 2H), 7.38 (m, 3H), 7.84 (d, 1H, J=9.0 Hz), 8.37 (m, 2H), 8.53 (m, 1H).

Sources & evidence

ORD record
ord-78862a23cc974e2abd4dedc0bbe1572f
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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