Potassium Carbonate → HCID 86727378, compound

HRID 519020Notes

Reaction equation

HRID 519020 reaction equation
[CH:1]([N:14]1[CH2:17][C:16]([NH:19][C:20]2[CH:21]=[C:22]3[C:31](=[CH:32][C:33]=2Br)[O:30][CH2:29][C:28]2[N:23]3[CH:24]([CH3:36])[C:25](=[O:35])[NH:26][N:27]=2)([CH3:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:43]1(B(O)O)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>O.O1CCOCC1.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]>[CH:1]([N:14]1[CH2:17][C:16]([NH:19][C:20]2[CH:21]=[C:22]3[C:31](=[CH:32][C:33]=2[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[O:30][CH2:29][C:28]2[N:23]3[CH:24]([CH3:36])[C:25](=[O:35])[NH:26][N:27]=2)([CH3:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 86727379HCID 86727379, compound

Product 1

HCID 86727378HCID 86727378, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A degassed mixture of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.175 g, 0.214 mmol), 6-(1-benzhydryl-3-methyl-azetidin-3-ylamino)-7-bromo-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.220 g, 0.403 mmol), K2CO3 (0.167 g, 1.208 mmol), and phenylboronic acid (0.123 g, 1.006 mmol) in water (0.5 mL) and dioxane (3 mL) was stirred at 100° C. overnight. The mixture was cooled to ambient temperature, the solution was concentrated in vacuo and the residue was purified by column chromatography on silica gel (eluting with 0 to 50% EtOAc in petroleum ether) to give 6-(1-benzhydryl-3-methyl-azetidin-3-ylamino)-4-methyl-7-phenyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.120 g, 55%). 1H NMR (CDCl3, 400 MHz): δ 8.09 (brs, 1H), 7.31 (m, 7H), 7.19 (m, 6H), 7.12 (m, 2H), 6.73 (s, 1H), 5.85 (s, 1H), 4.54 (q, J=6.8 Hz, 1H), 4.49 (d, J=12.8 Hz, 2H), 4.32 (s, 1H), 3.96 (brs, 1H), 3.22 (m, 2H), 2.93 (m, 2H), 1.52 (s, 3H), 1.37 (d, J=6.8 Hz, 3H).

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. concentrationthe solution was concentrated in vacuo
  3. customthe residue was purified by column chromatography on silica gel (eluting with 0 to 50% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-29671d162ea64d9aaed17e277de49c29
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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