Sodium Carbonate → HCID 58524996, compound

HRID 1944600Notes

Reaction equation

HRID 1944600 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[CH2:12][N:13]([CH3:40])[C:14](=[O:39])[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:41]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:44]=[C:43](B(O)O)[CH:42]=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>[CH3:40][N:13]1[CH2:12][C:6]2[CH:7]=[N:8][C:9]3[CH:10]=[CH:11][C:2]([C:43]4[CH:42]=[N:41][C:50]5[C:45]([CH:44]=4)=[CH:46][CH:47]=[CH:48][CH:49]=5)=[CH:3][C:4]=3[C:5]=2[N:15]([C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])[CH2:26][CH2:27]3)=[C:18]([C:35]([F:36])([F:38])[F:37])[CH:17]=2)[C:14]1=[O:39]

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 58524986HCID 58524986, compound

Product 1

HCID 58524996HCID 58524996, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 4-(4-(9-chloro-3-methyl-2-oxo-3,4-dihydropyrimido[5,4-c]quinolin-1(2H)-yl)-2-(trifluoromethyl)phenyl)piperazine-1-carboxylate (57 mg, 0.1 mmol) and quinolin-3-ylboronic acid (26 mg, 0.15 mmol) in 1,4-dioxane (2 mL) at room temperature was added bischloroditriphenylphosphine (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 12 h before cooling to room temperature. The reaction mixture was filtered through celite. The solvent was removed in vacuo and the resulting crude residue was purified by flash column chromatography to afford the title product 32 mg (47%). LC-MS: (M+H)=668.38

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customThe solvent was removed in vacuo
  3. customthe resulting crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-9a0eff2142c24ad7b4fb4f87ff94045a
Source dataset
uspto-grants-2013_03
Patent number
US08394818B2

Reaction notes

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