Dichloromethane → HCID 59627818, compound

HRID 1907844Notes

Reaction equation

HRID 1907844 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[N:10]=[N:9][N:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)[C:6]=2[N:7]=1.[O:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[O:28][CH2:29][CH2:30][N:31]1[CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=[N:32]1.C([O-])([O-])=O.[Cs+].[Cs+].C(Cl)Cl>COCCOC.O>[O:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[O:28][CH2:29][CH2:30][N:31]1[CH:35]=[C:34]([C:2]2[N:3]=[CH:4][C:5]3[N:10]=[N:9][N:8]([CH2:11][C:12]4[CH:13]=[C:14]5[C:19](=[CH:20][CH:21]=4)[N:18]=[CH:17][CH:16]=[CH:15]5)[C:6]=3[N:7]=2)[CH:33]=[N:32]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 44227707HCID 44227707, compoundHCID 593418191-[2-(oxan-2-yloxy)ethyl]-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 59627818HCID 59627818, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-((5-chloro-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)methyl)quinoline (393 mg, 1.33 mmol) in DME (8 mL) was added 1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (642 mg, 1.99 mmol) and Cs2CO3 (1.30 g, 3.98 mmol) in H2O (1.3 mL). The reaction mixture was degassed twice. The palladium catalyst Pd(dppf).CH2Cl2 (63 mg, 0.077 mmol) was added and the reaction mixture was degassed for two more times, and heated to 80° C. for 15 h under nitrogen. After cooling to room temperature, the solvent was removed under reduced pressure. Flash chromatography of the residue over silica gel, using 50% hexane in EtOAc to 100% EtOAc to 10% MeOH in EtOAc, gave the desired product (237 mg, 39%). 1H NMR (300 MHz, CDCl3) δ 1.23-1.82 (m, 6H), 3.42-4.59 (m, 7H), 6.04 (s, 2H), 7.41 (m, 1H), 7.82-7.85 (m, 1H), 7.90 (m, 1H), 8.08-8.15 (m, 2H), 8.31 (s, 1H), 8.34 (s, 1H), 8.90-8.92 (m, 1H), 9.46 (s, 1H); LCMS (APCI) m/z 457.2 (M+H+).

Workup

  1. customThe reaction mixture was degassed twice
  2. customthe reaction mixture was degassed for two more times
  3. temperatureAfter cooling to room temperature
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-47d82221afb745d5bafefd533a383feb
Source dataset
uspto-grants-2013_12
Patent number
US08598184B2

Reaction notes

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