Nitrogen → HCID 59402355, compound

HRID 2090394Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[CH:5][C:4](B2OC(C)(C)C(C)(C)O2)=[N:3]1.Br[C:17]1[CH:26]=[C:25]2[C:20]([CH2:21][CH:22]([CH3:41])[N:23]([C:27]3[CH:32]=[C:31]([N:33]4[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]4)[N:30]=[C:29]([NH2:40])[N:28]=3)[CH2:24]2)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+].N#N>O1CCOCC1.O.Cl[Pd](Cl)(P(C(C)(C)C)(C(C)(C)C)C1C=CC(N(C)C)=CC=1)P(C1C=CC(N(C)C)=CC=1)(C(C)(C)C)C(C)(C)C>[CH3:41][CH:22]1[CH2:21][C:20]2[C:25](=[CH:26][C:17]([C:4]3[CH:5]=[CH:6][N:2]([CH3:1])[N:3]=3)=[CH:18][CH:19]=2)[CH2:24][N:23]1[C:27]1[CH:32]=[C:31]([N:33]2[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]2)[N:30]=[C:29]([NH2:40])[N:28]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (11.5 mg, 0.0518 mmol), 4-(7-bromo-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine (0.018 g, 0.043 mmol) (Peak 1, Example 49, Step 7), dichloro(bis{di-tert-butyl[4-(dimethylamino)phenyl]phosphoranyl})palladium (0.916 mg, 0.00129 mmol), and sodium carbonate (9.14 mg, 0.0862 mmol) in 1,4-dioxane (0.50 mL) and water (0.10 mL) was vacuumed and refilled with N2 for 3 times and then stirred at 90° C. overnight. The mixture was purified by RP-HPLC (pH=10) to afford the desired product. LCMS (M+H)+: m/z=419.3.

Workup

customThe mixture was purified by RP-HPLC (pH=10)

Sources & evidence

ORD record: ord-744b5b395ea14806b18eba0c78594a22
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436008B2

Reaction notes

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