Dichloromethane → HCID 59402344, compound

HRID 2090472Notes

Reaction equation

HRID 2090472 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH:7]([CH3:26])[N:8]([C:12]3[CH:17]=[C:16]([N:18]4[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]4)[N:15]=[C:14]([NH2:25])[N:13]=3)[CH2:9]2)=[CH:4][CH:3]=1.[CH:27]1([N:30]2[CH2:38][C:37]3[C:32](=[CH:33][CH:34]=[C:35](B4OC(C)(C)C(C)(C)O4)[CH:36]=3)[C:31]2=[O:48])[CH2:29][CH2:28]1.C(=O)([O-])[O-].[K+].[K+].ClCCl>O1CCOCC1.O>[NH2:25][C:14]1[N:13]=[C:12]([N:8]2[CH:7]([CH3:26])[CH2:6][C:5]3[C:10](=[CH:11][C:2]([C:35]4[CH:36]=[C:37]5[C:32](=[CH:33][CH:34]=4)[C:31](=[O:48])[N:30]([CH:27]4[CH2:29][CH2:28]4)[CH2:38]5)=[CH:3][CH:4]=3)[CH2:9]2)[CH:17]=[C:16]([N:18]2[CH2:19][CH2:20][N:21]([CH3:24])[CH2:22][CH2:23]2)[N:15]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 594023174-(7-bromo-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-amineHCID 594023502-Cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one

Product 1

HCID 59402344HCID 59402344, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-(7-bromo-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine (0.0209 g, 0.0500 mmol), 2-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one (0.0194 g, 0.0650 mmol), in 1,4-dioxane (0.30 mL) was stirred at r.t. for 10 min. Potassium carbonate (27.6 mg, 0.200 mmol) in water (0.15 mL) was added. The mixture was degassed and refilled with nitrogen three times. [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (2.5 mg, 0.0030 mmol) was added The mixture was degassed and refilled with nitrogen three times, and heated at 120° C.) (oil bath temperature) for 1 h. After cooling, the mixture was diluted with methanol, and filtered. The filtrate was purified on RP-HPLC (pH=10) to afford the desired product. LCMS (M+H)+: m/z=510.2.

Workup

  1. customThe mixture was degassed
  2. additionrefilled with nitrogen three times
  3. customwas degassed
  4. additionrefilled with nitrogen three times
  5. temperatureAfter cooling
  6. additionthe mixture was diluted with methanol
  7. filtrationfiltered
  8. customThe filtrate was purified on RP-HPLC (pH=10)

Sources & evidence

ORD record
ord-a881628a69fb4a0ba77bcd0372bd727b
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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