Sodium Carbonate → Ethyl 2-(4-(8-morpholino-2-(quinolin-2-ylethynyl)imidazo[1,2-a]pyrazin-5-yl)-1H-pyrazol-1-yl)acetate

HRID 1772720Notes

Reaction equation

HRID 1772720 reaction equation
Br[C:2]1[N:7]2[CH:8]=[C:9]([C:11]#[C:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[N:10]=[C:6]2[C:5]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[N:4][CH:3]=1.[CH2:29]([O:31][C:32](=[O:48])[CH2:33][N:34]1[CH:38]=[C:37](B2OC(C)(C)C(C)(C)O2)[CH:36]=[N:35]1)[CH3:30].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.[CH-]1C=C(P(C2C=CC=CC=2)C2C=CC=CC=2)C=C1.[CH-]1C=C(P(C2C=CC=CC=2)C2C=CC=CC=2)C=C1.Cl[Pd]Cl.[Fe+2]>[O:26]1[CH2:27][CH2:28][N:23]([C:5]2[C:6]3[N:7]([CH:8]=[C:9]([C:11]#[C:12][C:13]4[CH:22]=[CH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[N:14]=4)[N:10]=3)[C:2]([C:37]3[CH:36]=[N:35][N:34]([CH2:33][C:32]([O:31][CH2:29][CH3:30])=[O:48])[CH:38]=3)=[CH:3][N:4]=2)[CH2:24][CH2:25]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 162183851-(Ethoxycarbonylmethyl)-1H-pyrazole-4-boronic acid pinacol esterHCID 1177323014-(5-Bromo-2-(quinolin-2-ylethynyl)imidazo[1,2-a]pyrazin-8-yl)morpholine

Product 1

HCID 117728270Ethyl 2-(4-(8-morpholino-2-(quinolin-2-ylethynyl)imidazo[1,2-a]pyrazin-5-yl)-1H-pyrazol-1-yl)acetate

Reagents, catalysts & solvents 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of compound 80b (100 mg, 0.230 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-Pyrazole-1-acetic acid ethyl ester (129 mg, 0.460 mmol), dichloro(1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloromethane adduct (17.0 mg, 0.0230 mmol), and 1M sodium carbonate (1.15 mL, 1.15 mmol) in dioxane (4 mL) under and Argon gas atmosphere was heated to 80° C. for 1 h. After cooling, the reaction mixture was filtered through a pad of diatomaceous earth and concentrated under reduced pressure. The resulting residue was purified by preparative TLC (EtOAc/CH2Cl2; 7:3, v/v) to give compound 80c. Mass Spectrum (LCMS, ESI pos.): Calcd. for C28H25N2O3: 508.2 (M+H). found: 508.5.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered through a pad of diatomaceous earth
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by preparative TLC (EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-9c2c104aa54c4bd8a1ca9e71ceea30dc
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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