Potassium Phosphate, Tribasic → HCID 77845924, compound

HRID 595583Notes

Reaction equation

HRID 595583 reaction equation
[C:1]1([C:6]2[O:7][C:8]3[CH:18]=[C:17]([N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])[C:16](B4OC(C)(C)C(C)(C)O4)=[CH:15][C:9]=3[C:10]=2[C:11]([NH:13][CH3:14])=[O:12])[CH2:5][CH2:4][CH2:3][CH:2]=1.Cl[C:35]1[CH:36]=[CH:37][C:38]2[O:50][CH2:49][N:41]3[C:42]4[CH:43]=[CH:44][CH:45]=[CH:46][C:47]=4[CH:48]=[C:40]3[C:39]=2[N:51]=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>[C:1]1([C:6]2[O:7][C:8]3[CH:18]=[C:17]([N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])[C:16]([C:35]4[CH:36]=[CH:37][C:38]5[O:50][CH2:49][N:41]6[C:42]7[CH:43]=[CH:44][CH:45]=[CH:46][C:47]=7[CH:48]=[C:40]6[C:39]=5[N:51]=4)=[CH:15][C:9]=3[C:10]=2[C:11]([NH:13][CH3:14])=[O:12])[CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 86728227HCID 86728227, compoundHCID 90333862HCID 90333862, compound

Product 1

HCID 77845924HCID 77845924, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a degassed solution of 2-(cyclopent-1-en-1-yl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (110 mg, 0.23 mmol), 2-chloro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole (70 mg, 0.27 mmol), K3PO4(123 mg, 0.46 mmol) in 1,4-Dioxane (5 mL) and H2O (0.5 ml) was added Pd(dba)3 (5 mg) and X-Phos (5 mg) under N2, then the mixture was stirred at 110° C. for 2 hours. The reaction mixture was cooled to RT and filtered. The filtrate was washed with H2O, brine, extract with DCM, and dried over Na2SO4. After concentration, the residue was purified by prep-HPLC to give the product of 2-(cyclopent-1-en-1-yl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)benzofuran-3-carboxamide (30 mg, yield: 23%). 1H-NMR (CDCl3, 400 MHz) δ 7.88 (s, 1H), 7.69 (d, J=7.6 Hz, 1H), 7.56 (s, 1H), 7.47 (s, 2H), 7.27˜7.33 (m, 2H), 7.14˜7.20 (m, 2H), 6.74 (s, 1H), 6.10 (s, 1H), 5.99 (s, 2H), 3.32 (s, 3H), 3.01 (d, J=4.8 Hz, 3H), 2.83 (d, J=6.8 Hz, 2H), 2.73 (s, 3H), 2.62 (t, J=6.8 Hz, 2H), 2.00˜2.08 (m, 2H). MS (M+H)+: 569.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. filtrationfiltered
  3. washThe filtrate was washed with H2O, brine
  4. extractionextract with DCM
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentration
  7. customthe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-cccc7c34c6ef4baf929669831ea62b65
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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