2-Chloropyridine-5-boronic acid → HCID 86661677, compound

HRID 1262081Notes

Reaction equation

HRID 1262081 reaction equation
Br[C:2]1[N:10]2[C:5]([CH:6]=[N:7][C:8]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH2:23][CH2:22][CH:21]([N:24]5[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]5)[CH2:20][CH2:19]4)=[CH:14][C:13]=3[O:31][CH3:32])=[N:9]2)=[CH:4][CH:3]=1.[Cl:33][C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][N:35]=1>>[Cl:33][C:34]1[N:35]=[CH:36][C:37]([C:2]2[N:10]3[C:5]([CH:6]=[N:7][C:8]([NH:11][C:12]4[CH:17]=[CH:16][C:15]([N:18]5[CH2:19][CH2:20][CH:21]([N:24]6[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]6)[CH2:22][CH2:23]5)=[CH:14][C:13]=4[O:31][CH3:32])=[N:9]3)=[CH:4][CH:3]=2)=[CH:38][CH:39]=1

Participants

3

Reactant 2

HCID 38450342-Chloropyridine-5-boronic acidHCID 66711255(7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-{2-methoxy-4-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-phenyl}-amine

Product 1

HCID 86661677HCID 86661677, compoundYield 23%

Conditions

Temperature
80 °C

Procedure

Following the example of 532 (D), (7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-{2-methoxy-4-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-phenyl}-amine (0.088 g, 0.00018 mol) and 2-Chloro-5-pyridineboronic acid (0.028 g, 0.00018 mol) were heated at 80° C. overnight. Purification by Gilson chromatography gave [7-(6-Chloro-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-{2-methoxy-4-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-phenyl}-amine (0.022 g, 23%) as a tan solid. MP: 186-188° C.; 1H-NMR (DMSO-d6, 400 MHz) δ 9.18-9.17 (d, 1H, J=2.40 Hz), 8.98 (s, 1H), 8.64-8.61 (d, 1H, J=5.88 Hz), 8.05 (s, 1H), 7.61 (s, 1H), 7.59 (s, 1H), 7.34-7.32 (d, 1H, J=4.80 Hz), 6.97-6.95 (d, 1H, J=4.84 Hz), 6.77 (br, 1H), 6.63 (br, 1H), 3.83 (s, 1H), 3.46 (br, 2H), 2.78 (br, 2H), 2.08-2.01 (br, 3H), 1.66 (m, 2H).

Workup

  1. customPurification by Gilson chromatography

Sources & evidence

ORD record
ord-84821524e77f4b6f98e5c68af679711f
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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