Potassium Phosphate, Tribasic → HCID 86728247, compound

HRID 1776841Notes

Reaction equation

HRID 1776841 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[O:21][CH2:20][N:8]3[C:9]4[CH:10]=[CH:11][CH:12]=[C:13]([C:16]([O:18][CH3:19])=[O:17])[C:14]=4[CH:15]=[C:7]3[C:6]=2[N:22]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[O:31][C:32]3[CH:42]=[C:41]([N:43]([CH3:48])[S:44]([CH3:47])(=[O:46])=[O:45])[C:40](B4OC(C)(C)C(C)(C)O4)=[CH:39][C:33]=3[C:34]=2[C:35]([NH:37][CH3:38])=[O:36])=[CH:26][CH:25]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[O:31][C:32]3[CH:42]=[C:41]([N:43]([CH3:48])[S:44]([CH3:47])(=[O:45])=[O:46])[C:40]([C:2]4[CH:3]=[CH:4][C:5]5[O:21][CH2:20][N:8]6[C:9]7[CH:10]=[CH:11][CH:12]=[C:13]([C:16]([O:18][CH3:19])=[O:17])[C:14]=7[CH:15]=[C:7]6[C:6]=5[N:22]=4)=[CH:39][C:33]=3[C:34]=2[C:35](=[O:36])[NH:37][CH3:38])=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 682394022-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamideHCID 86728248HCID 86728248, compound

Product 1

HCID 86728247HCID 86728247, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a degassed solution of methyl 2-chloro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole-11-carboxylate (40 mg, 0.13 mmol) and 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (50 mg, 0.10 mmol) in 1,4-dioxane (3 mL), Pd2(dba)3 (10 mg), X-Phos (10 mg) and K3PO4 (60 mg, 0.23 mmol) were added under N2. The mixture was heated to 100° C. for 2 hours. The reaction mixture was cooled to RT, filtered and washed with EtOAc. The filtrate was washed with H2O, brine, dried over Na2SO4. After concentrated, the resulting residue was purified using column chromatography (dichloromethane:MeOH=100:1) to provide the product of methyl 2-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole-11-carboxylate (55 mg, yield: 84%). MS (M+H)+: 655.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. filtrationfiltered
  3. washwashed with EtOAc
  4. washThe filtrate was washed with H2O, brine
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentrated
  7. customthe resulting residue was purified

Sources & evidence

ORD record
ord-51f20e9d0b58426e9a16ca697ba64b2e
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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