Potassium Phosphate, Tribasic → HCID 58255779, compound

HRID 1695789Notes

Reaction equation

HRID 1695789 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH3:11])=[C:4]([NH:12][C:13]([C:15]2[N:16]=[C:17]([CH2:20][N:21]3[CH2:26][C@H:25]([CH3:27])[O:24][C@H:23]([CH3:28])[CH2:22]3)[S:18][CH:19]=2)=[O:14])[CH:3]=1.[F:29][C:30]1[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=1[S:37]([NH:40][C:41]1[C:42]([O:56][CH3:57])=[N:43][CH:44]=[C:45](B2OC(C)(C)C(C)(C)O2)[CH:46]=1)(=[O:39])=[O:38].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O.O1CCOCC1.C(=O)=O.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]>[F:29][C:30]1[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=1[S:37]([NH:40][C:41]1[CH:46]=[C:45]([C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[N:7][N:8]3[CH3:11])=[C:4]([NH:12][C:13]([C:15]3[N:16]=[C:17]([CH2:20][N:21]4[CH2:26][C@H:25]([CH3:27])[O:24][C@H:23]([CH3:28])[CH2:22]4)[S:18][CH:19]=3)=[O:14])[CH:3]=2)[CH:44]=[N:43][C:42]=1[O:56][CH3:57])(=[O:39])=[O:38]

Participants

8

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 58255792HCID 58255792, compoundHCID 595647052,4-difluoro-N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide

Product 1

HCID 58255779HCID 58255779, compoundYield 25.7%

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 280Carbon DioxideSolventHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
100 °C

Procedure

N-(6-Bromo-1-methyl-1H-indazol-4-yl)-2-{[(2R,6S)-2,6-dimethyl-4-morpholinyl]methyl}-1,3-thiazole-4-carboxamide (50 mg, 0.108 mmol), 2,4-difluoro-N-[2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl]benzenesulfonamide (46 mg, 0.108 mmol), Pd(dppf)Cl2 (16 mg, 0.022 mmol) and tripotassium phosphate (69 mg, 0.323 mmol) were added to 1,4-dioxane (1 ml) and water (0.25 ml) then put in the microwave. The reaction mixture was heated at 100° C. for 20 min. The solvent was blown down to give a brown oil which was dissolved in water (1 ml) and dioxane (1 ml), put in cardice for 15 min then put on freeze dryer to give a brown solid which was purified by MDAP (Method E) to give the title compound as a white solid (19 mg).

Workup

  1. customto give a brown oil which
  2. customto give a brown solid which
  3. customwas purified by MDAP (Method E)

Sources & evidence

ORD record
ord-8dceaed395084550b942cee6b38717c5
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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