Sodium Carbonate → HCID 90412802, compound

HRID 1522041Notes

Reaction equation

HRID 1522041 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)=[CH:10][C:3]=12.C(OC([NH:31][C:32]1[CH:37]=[C:36](B(O)O)[C:35]([Cl:41])=[CH:34][N:33]=1)=O)(C)(C)C.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C(OCC)(=O)C.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.C(Cl)Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:31][C:32]1[CH:37]=[C:36]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[NH:8][C:9]([CH:11]4[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:18])[CH2:15][CH2:16]4)=[CH:10][C:3]=23)[C:35]([Cl:41])=[CH:34][N:33]=1

Participants

10

Reactant 5

HCID 10340Sodium CarbonateHCID 10796Cesium carbonateHCID 75806TricyclohexylphosphineHCID 67043210HCID 67043210, compoundHCID 90408209HCID 90408209, compound

Product 1

HCID 90412802HCID 90412802, compound

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 178478482HCID 178478482, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of Example 17E (565 mg, 1.682 mmol), (2-((tert-butoxycarbonyl)amino)-5-chloropyridin-4-yl)boronic acid (550 mg, 2.02 mmol), (PPh3)2PdCl2—CH2Cl2 adduct (70.9 mg, 0.10 mmol), tricyclohexylphosphine (28.3 mg, 0.10 mmol), Pd(dppf)2Cl2 (82 mg, 0.10 mmol), cesium carbonate (1.64 g, 5.05 mmol) and 1M Na2CO3 aqueous solution (5.05 mL, 5.05 mmol) in dioxane (18 mL) in a sealed tube was heated at 10° C. for 3 days. After cooling, the reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was concentrated and the residue was purified by reverse phase chromatography (C18 column), eluted with a gradient of 10%-70% acetonitrile in 0.1% TFA water solution to provide the title compound. LC/MS: 428 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. washwashed with brine
  3. concentrationThe organic layer was concentrated
  4. customthe residue was purified by reverse phase chromatography (C18 column)
  5. washeluted with a gradient of 10%-70% acetonitrile in 0.1% TFA water solution

Sources & evidence

ORD record
ord-91edc03e854c44a8a88adf7dac74a6d9
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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