Potassium Phosphate, Tribasic → HCID 71295546, compound

HRID 1776829Notes

Reaction equation

HRID 1776829 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:24])=[O:23])[C:18](B4OC(C)(C)C(C)(C)O4)=[CH:17][C:11]=3[C:12]=2[C:13]([NH:15][CH3:16])=[O:14])=[CH:4][CH:3]=1.Cl[C:37]1[CH:38]=[CH:39][C:40]2[O:53][CH2:52][N:43]3[C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][C:49]=4[C:50]([Cl:51])=[C:42]3[C:41]=2[N:54]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>O1CCOCC1.O.CCOC(C)=O.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]>[Cl:51][C:50]1[C:49]2[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=2[N:43]2[CH2:52][O:53][C:40]3[CH:39]=[CH:38][C:37]([C:18]4[C:19]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][C:10]5[O:9][C:8]([C:5]6[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=6)=[C:12]([C:13]([NH:15][CH3:16])=[O:14])[C:11]=5[CH:17]=4)=[N:54][C:41]=3[C:42]=12

Participants

8

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 86728239HCID 86728239, compound

Product 1

HCID 71295546HCID 71295546, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

To a degassed solution of 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (110 mg, 0.22 mmol), 2,12-dichloro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole (64 mg, 0.22 mmol) and K3PO4 (176 mg, 0.66 mmol) in dioxane/H2O (0.8 mL/0.2 mL) was added Pd2(dba)3 (10 mg, 0.01 mmol) and X-Phos (10 mg, 0.02 mmol) under N2. The mixture was heated to 80° C. and then stirred for 1 hour. The reaction mixture was cooled to RT, diluted with EtOAc and filtered. The filtrate was washed with H2O, brine, dried over Na2SO4. After concentrated, the resulting residue was purified using prep-TLC (petroleum ether:EtOAc=1:1) to provide the desired product of compound 55 (60 mg, yield: 43.2%). 1H-NMR (CDCl3, 400 MHz) δ 8.13 (s, 1H), 7.94˜7.98 (m, 2H), 7.65 (d, J=8.0 Hz, 1H), 7.58 (s, 1H), 7.53 (d, J=8.4 Hz, 1H), 7.42 (d, J=8.4 Hz, 1H), 7.28˜7.31 (m, 2H), 7.11˜7.20 (m, 3H), 5.85˜5.95 (br s, 3H), 3.32 (s, 3H), 2.96 (d, J=4.8 Hz, 3H), 2.72 (s, 3H). MS (M+H)+: 631.

Workup

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

Sources & evidence

ORD record
ord-51beaa7f614b4354be889d2318ead4a3
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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