Sodium Carbonate → HCID 86613122, compound

HRID 1432330Notes

Reaction equation

HRID 1432330 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17](Br)[CH:18]=[C:13]3[C:12]([C:20]#[C:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:28][N:29]([C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1)[CH3:30].[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>CCO.C1(C)C=CC=CC=1.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>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:34]4[CH:35]=[CH:36][C:31]([N:29]([CH3:30])[CH3:28])=[CH:32][CH:33]=4)[CH:18]=[C:13]3[C:12]([C:20]#[C:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 27343444-(Dimethylamino)phenylboronic acidHCID 68949292HCID 68949292, compound

Product 1

HCID 86613122HCID 86613122, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of acetylene 20 (53 mg, 0.121 mmol), 4-(N,N-dimethylamino)phenylboronic acid (30 mg, 0.182 mmol), PdCl2(PPh3)2 (9.0 mg, 0.012 mmol), LiCl (15 mg, 0.363 mmol) and 1.0 M aq. Na2CO3 (300 μL, 0.302 mmol) in EtOH (2 mL) and toluene (2 mL) was stirred for 2 h 45 min. at 105° C. The reaction mixture was then poured onto brine (5 mL) and extracted with ethyl acetate (4×10 mL) and the combined organic extracts dried (MgSO4) and concentrated. The residue was purified by preparative LCMS (column LUNA 10μ C18(2) 00G-4253-V0 250×50 mm) using water-acetonitrile (0.1% AcOH) as eluent (in gradient; flow 80 mL/min) to give product 21 as a yellow solid (36.85 mg, 64%); 1H NMR (400 MHz, CDCl3) δ 3.01 (s, 6H), 6.82 (d, J=8.82 Hz, 2H), 7.35-7.42 (m, 3H), 7.45-7.65 (m, 7H), 7.95 (s, 1H), 8.08 (d, J=2.14 Hz, 1H), 8.23 (m, 2H), 8.68 (d, J=2.13 Hz, 1H).

Workup

  1. additionThe reaction mixture was then poured onto brine (5 mL)
  2. extractionextracted with ethyl acetate (4×10 mL)
  3. dry with materialthe combined organic extracts dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by preparative LCMS (column LUNA 10μ C18(2) 00G-4253-V0 250×50 mm)

Sources & evidence

ORD record
ord-6e9b42d04f4c4dcfb723d9b8982e2946
Source dataset
uspto-grants-2009_11
Patent number
US07612086B2

Reaction notes

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