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Sodium Carbonate → 1-(4-benzylphenyl)-9-(4-hydroxyphenyl)benzo[h][1,6]naphthyridin-2(1H)one

HRID 336872
Notes
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Reaction equation

HRID 336872 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:23]3[C:18](=[CH:19][N:20]=[C:21]4[CH:27]=[CH:26][C:25](Cl)=[CH:24][C:22]4=3)[CH:17]=[CH:16][C:15]2=[O:29])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.C([O-])([O-])=O.[Na+].[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C>O1CCOCC1.CCO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:23]3[C:18](=[CH:19][N:20]=[C:21]4[CH:27]=[CH:26][C:25]([C:34]5[CH:35]=[CH:36][C:31]([OH:30])=[CH:32][CH:33]=5)=[CH:24][C:22]4=3)[CH:17]=[CH:16][C:15]2=[O:29])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneHCID 585249781-(4-benzylphenyl)-9-chlorobenzo[h][1,6]naphthyridin-2(1H)-one

Product 1

HCID 461916921-(4-benzylphenyl)-9-(4-hydroxyphenyl)benzo[h][1,6]naphthyridin-2(1H)one
Yield 64%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-(4-benzylphenyl)-9-chlorobenzo[h][1,6]naphthyridin-2(1H)-one (100 mg, 0.22 mmol) in 1,4-dioxane (0.6 mL) was added 4-hydroxyphenylboronic acid (45 mg, 0.33 mmol) and 1 N Na2CO3 (0.66 mL, 0.66 mmol). The reaction mixture was degassed using Argon gas for 10 min and added Pd(PPh3)2Cl2 (15 mg, 0.02 mmol) and di-tert-butyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (15 mg, 0.04 mmol). The reaction flask was put into the preheated oil-bath at 100° C. The reaction mixture was further stirred at 100° C. a period of 8 hours after which, it was filtered and partitioned between ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over Mg504, filtered and concentrated. The crude product was purified by flash column chromatography using a 97:3 v/v CH2Cl2:EtOH as solvent to afford title compound (64 mg, 64% yield) as a yellow solid. 1H NMR 600 MHz (CDCl3) δ 9.08 (s, 1H), 8.42 (s, 1H), 8.04 (d, J=2.4 Hz, 1H), 7.95 (d, J=8.2 Hz, 1H), 7.61 (dd, J=2.1, 6.6 Hz, 1H), 7.25 (m, 2H), 7.12 (m, 4H), 7.00 (m, 5H), 6.75 (d, J=8.4 Hz, 2H), 6.48 (dd, J=2.4, 6.2 Hz, 1H), 3.88 (s, 2H), MS m/z: 455.27 (M+1).

Workup

  1. customThe reaction mixture was degassed
  2. customfor 10 min
  3. customwas put into the preheated oil-bath at 100° C
  4. filtrationwas filtered
  5. custompartitioned between ethyl acetate and water
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. washThe combined organic extracts were washed with brine
  9. customdried over Mg504
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-bd09652d47ef44b8936d5ca95e6ca3b1
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889706B2

Reaction notes

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