Potassium Phosphate, Tribasic → HCID 117771663, compound

HRID 2201562Notes

Reaction equation

HRID 2201562 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]2=[O:18].[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[O:27][C:28]3[CH:38]=[C:37]([N:39]([CH3:44])[S:40]([CH3:43])(=[O:42])=[O:41])[C:36](B4OC(C)(C)C(C)(C)O4)=[CH:35][C:29]=3[C:30]=2[C:31]([NH:33][CH3:34])=[O:32])=[CH:22][CH:21]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=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:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[O:27][C:28]3[CH:38]=[C:37]([N:39]([CH3:44])[S:40]([CH3:43])(=[O:41])=[O:42])[C:36]([C:2]4[CH:3]=[C:4]5[C:9](=[CH:10][CH:11]=4)[N:8]=[CH:7][N:6]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:5]5=[O:18])=[CH:35][C:29]=3[C:30]=2[C:31]([NH:33][CH3:34])=[O:32])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 44203112HCID 44203112, compoundHCID 682394022-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide

Product 1

HCID 117771663HCID 117771663, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a degassed mixture of 6-bromo-3-phenylquinazolin-4(3H)-one (150 mg, 0.498 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 (100 mg, 0.199 mmol) in N,N-dimethyl-formamide (4 mL) were added Pd(dppf)Cl2 (15 mg) and K3PO4 (211 mg, 0.994 mmol) under N2. After being heated to 90° C. overnight, the reaction mixture was cooled to RT and filtered. The filtrate was concentrated and the residue was purified by prep-HPLC to give the product of 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4-oxo-3-phenyl-3,4-dihydroquinazolin-6-yl)benzofuran-3-carboxamide (10.28 mg, yield: 10%). 1H-NMR (CDCl3, 400 MHz) δ 8.41 (d, J=2.0 Hz, 1H), 8.31 (s, 1H), 7.99˜7.92 (m, 3H), 7.88 (t, J=3.6 Hz, 2H), 7.64 (s, 1H), 7.60˜7.52 (m, 3H), 7.46 (d, J=7.2 Hz, 2H), 7.21 (t, J=8.8 Hz, 2H), 5.96 (d, J=4.8 Hz, 1H), 3.18 (s, 3H), 3.00 (d, J=5.2 Hz, 3H), 2.79 (s, 3H). MS (M+H)+: 597.

Workup

  1. temperaturethe reaction mixture was cooled to RT
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-f87be3463f3d4de1837312f9392935e1
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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