Sodium Carbonate → HCID 178461413, compound

HRID 2390424Notes

Reaction equation

HRID 2390424 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:20])=[C:7]([CH2:12][CH2:13][N:14]3[CH2:18][CH2:17][CH2:16][C@H:15]3[CH3:19])[N:8]=[N:9]2)=[CH:4][CH:3]=1.[C:21]([C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)#[N:22].C([O-])([O-])=O.[Na+].[Na+]>C(O)(C)C.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>[OH:20][C:6]1[C:5]2[C:10](=[CH:11][C:2]([C:26]3[CH:27]=[CH:28][C:23]([C:21]#[N:22])=[CH:24][CH:25]=3)=[CH:3][CH:4]=2)[N:9]=[N:8][C:7]=1[CH2:12][CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][C@H:15]1[CH3:19]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 178461412HCID 178461412, compound

Product 1

HCID 178461413HCID 178461413, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of the product from Example 168D (0.30 g, 0.805 mmol), 4-cyanophenylboronic acid (0.15 g, 1.05 mmol), Pd(PPh3)2Cl2 (0.03 g, 0.04 mmol), and 1 M Na2CO3 (2.01 mL, 2.01 mmol) in isopropanol (15 mL) was heated to 90° C. under a dry nitrogen atmosphere for 2 days. After cooling, the reaction mixture was filtered through celite and concentrated under reduced pressure. The crude material was purified by column chromatography (100% dichloromethane to 90:10 dichloromethane/methanol) to afford the product in 33% yield as a light brown solid. 1H NMR (CD3OD, 300 MHz) δ 8.29 (d, J=9 Hz, 1H), 7.95 (q, J=9 Hz, 4H), 7.83 (d, J=3 Hz, 1H), 7.75 (dd, J=3, 9 Hz, 1H), 3.49-3.42 (m, 2H), 3.17-3.12 (m, 2H), 2.78-2.73 (m, 2H), 2.62-2.59 (m, 1H), 2.12-2.09 (m, 1H), 1.92-1.84 (m, 2H), 1.61-1.53 (m, 1H), 1.25 (d, J=6 Hz, 3H). MS (ESI) [M+H]+ at 359.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered through celite and
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material was purified by column chromatography (100% dichloromethane to 90:10 dichloromethane/methanol)
  5. customto afford the product in 33% yield as a light brown solid

Sources & evidence

ORD record
ord-fb3f271f7c7348938c7394a475656164
Source dataset
uspto-grants-2012_09
Patent number
US08273767B2

Reaction notes

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