Sodium Carbonate → HCID 58524960, compound

HRID 1944597Notes

Reaction equation

HRID 1944597 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[CH2:12][O:13]C(=O)[N:15]([C:16]4[CH:21]=[CH:20][C:19]([N:22]5[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]5)=[C:18]([C:35]([F:38])([F:37])[F:36])[CH:17]=4)[C:5]=3[C:4]=2[CH:3]=1.[N:40]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:43]=[C:42](B(O)O)[CH:41]=1.CC(C1C=C(C(C)C)C(C2C(P(C(C)(C)C)C(C)(C)C)=CC=CC=2)=C(C(C)C)C=1)C.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[C:31]([O:30][C:28]([N:25]1[CH2:26][CH2:27][N:22]([C:19]2[CH:20]=[CH:21][C:16]([NH:15][C:5]3[C:4]4[C:9](=[CH:10][CH:11]=[C:2]([C:42]5[CH:41]=[N:40][C:49]6[C:44]([CH:43]=5)=[CH:45][CH:46]=[CH:47][CH:48]=6)[CH:3]=4)[N:8]=[CH:7][C:6]=3[CH2:12][OH:13])=[CH:17][C:18]=2[C:35]([F:38])([F:36])[F:37])[CH2:23][CH2:24]1)=[O:29])([CH3:32])([CH3:33])[CH3:34]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 2734663Quinoline-3-boronic acidHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneHCID 46191440HCID 46191440, compound

Product 1

HCID 58524960HCID 58524960, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 4-(4-(9-chloro-2-oxo-2H-[1,3]oxazino[5,4-c]quinolin-1(4H)-yl)-2-(trifluoromethyl)phenyl)piperazine-1-carboxylate (56 mg, 0.1 mmol) and quinolin-3-ylboronic acid (25 mg, 0.15 mmol) in 1,4-dioxane (1 mL) at room temperature was added bischloroditriphenyl phosphine palladium (4 mg, 0.005 mmol), tert-butyl Xphos (4 mg, 0.01 mmol), and Na2CO3(0.3 mL, 0.3 mmol). The resultant solution was heated to 100° C. for 4 h and then allowed to cool to room temperature, filtered through celite, and washed with EtOAc (3×10 mL). After removal of solvent in vacuo, the residue was purified by flash column chromatography to afford the title compound (35 mg, 55%). LC-MS: (M+H)=630.30

Workup

  1. filtrationfiltered through celite
  2. washwashed with EtOAc (3×10 mL)
  3. customAfter removal of solvent in vacuo
  4. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-b006f20eee1a41c490bc0a12479c247c
Source dataset
uspto-grants-2013_03
Patent number
US08394818B2

Reaction notes

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