Sodium Carbonate → HCID 50991008, compound

HRID 1499027Notes

Reaction equation

HRID 1499027 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[C:5]2[O:10][C:9]3[N:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:8]=3[C:6]=2[N:7]=1.[NH:22]1[C:30]2[CH:29]=[CH:28][CH:27]=[C:26](B(O)O)[C:25]=2[CH:24]=[CH:23]1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH:22]1[C:30]2[C:25](=[C:26]([C:2]3[N:3]=[C:4]([N:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)[C:5]4[O:10][C:9]5[N:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:8]=5[C:6]=4[N:7]=3)[CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27631731H-Indole-4-boronic acidHCID 86667797HCID 86667797, compound

Product 1

HCID 50991008HCID 50991008, compoundYield 16%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-chloro-7-methyl-4-morpholin-4-yl-pyrido[3′,2′:4,5]furo[3,2-d]pyrimidine, 18 (27 mg, 0.09 mmol, leg), indole-4-boronic acid (43 mg, 0.27 mmol, 3 eq) and PdCl2(PPh3)2 (12.4 mg, 0.02 mmol, 20 mol%) in a mixture of dioxane (2 mL) and H2O (1.0 mL) was added Na2CO3 (19 mg, 0.18 mmol, 2 eq) under Ar(g). The reaction mixture was then heated in a pressure tube for 18 h at 90° C. Once cooled down, the mixture was partitioned with H2O (10 mL) and extracted with CH2Cl2 (2×10 mL) and EtOAc (2×10 mL). The combined organic extracts were dried over MgSO4 and the solvent was removed in vacuo. The residue was further purified by SCX-3 cartridge eluting with CH2Cl2/MeOH (1:0-0:1 then +1M NH3) followed by silica gel column chromatography with hexane/EtOAc (3:1-0:1) to yield N as a pale brown solid (5.4 mg, 16%).

Workup

  1. temperatureOnce cooled down
  2. customthe mixture was partitioned with H2O (10 mL)
  3. extractionextracted with CH2Cl2 (2×10 mL) and EtOAc (2×10 mL)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. customthe solvent was removed in vacuo
  6. customThe residue was further purified by SCX-3 cartridge
  7. washeluting with CH2Cl2/MeOH (1:0-0:1

Sources & evidence

ORD record
ord-38a5da35e50a44729168752d62e71be2
Source dataset
uspto-grants-2015_12
Patent number
US09200007B2

Reaction notes

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