Potassium Phosphate, Tribasic → HCID 71295625, compound

HRID 1776813Notes

Reaction equation

HRID 1776813 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:16]2[NH:25][C:19]3=[CH:20][N:21]=[CH:22][C:23]([F:24])=[C:18]3[CH:17]=2)=[N:11][C:12](Cl)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[O:34][C:35]3[CH:45]=[C:44]([N:46]([CH3:51])[S:47]([CH3:50])(=[O:49])=[O:48])[C:43](B4OC(C)(C)C(C)(C)O4)=[CH:42][C:36]=3[C:37]=2[C:38]([NH:40][CH3:41])=[O:39])=[CH:29][CH:28]=1.[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].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:43]2[C:44]([N:46]([CH3:51])[S:47]([CH3:50])(=[O:49])=[O:48])=[CH:45][C:35]3[O:34][C:33]([C:30]4[CH:31]=[CH:32][C:27]([F:26])=[CH:28][CH:29]=4)=[C:37]([C:38]([NH:40][CH3:41])=[O:39])[C:36]=3[CH:42]=2)=[N:11][C:10]=1[C:16]1[NH:25][C:19]2=[CH:20][N:21]=[CH:22][C:23]([F:24])=[C:18]2[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 682394022-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamideHCID 86728232HCID 86728232, compound

Product 1

HCID 71295625HCID 71295625, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a degassed solution of 2-(3-(benzyloxy)-6-chloropyridin-2-yl)-4-fluoro-1H-pyrrolo[2,3-c]pyridine (300 mg, 0.85 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 (387 mg, 0.77 mmol) in 1,4-dioxane (5.0 mL) was added Pd2(dba)3 (10 mg), X-Phos (10 mg) and K3PO4 (452 mg, 1.70 mmol) under N2. The mixture was heated at 100° C. for 3 hours. The reaction mixture was cooled to room temperature and filtered. The filtrate was washed with H2O, brine, dried over Na2SO4. After it was concentrated, the resulting residue was purified using column (petroleum ether:EtOAc=2:1) to provide 5-(5-(benzyloxy)-6-(4-fluoro-1H-pyrrolo[2,3-c]pyridin-2-yl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (165 mg, yield: 31%). 1H-NMR (CDCl3, 400 MHz) δ 10.73 (s, 1H), 8.49 (s, 1H), 7.99 (d, J=8.0 Hz, 2H), 7.92 (dd, J=8.0, 8.0 Hz, 2H), 7.50˜7.45 (m, 3H), 7.43˜7.40 (m, 5H), 7.16 (t, J=8.0 Hz, 2H), 6.56 (s, 1H), 5.32 (s, 12H), 3.10 (s, 3H), 2.91 (d, J=4.0 Hz, 3H), 2.80 (s, 3H). MS (M+H)+: 694.

Workup

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

Sources & evidence

ORD record
ord-6131a9b2627440bc802aaf841674dd5f
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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