Sodium Carbonate → HCID 178419025, compound

HRID 900208Notes

Reaction equation

HRID 900208 reaction equation
Br[C:2]1[CH:18]=[CH:17][C:5]2[NH:6][C:7]([CH2:9][CH2:10][N:11]3[CH2:15][CH2:14][CH2:13][CH:12]3[CH3:16])=[N:8][C:4]=2[CH:3]=1.[C:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)#[N:20].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:16][C@@H:12]1[CH2:13][CH2:14][CH2:15][N:11]1[CH2:10][CH2:9][C:7]1[NH:6][C:5]2[CH:17]=[CH:18][C:2]([C:24]3[CH:25]=[CH:26][C:21]([C:19]#[N:20])=[CH:22][CH:23]=3)=[CH:3][C:4]=2[N:8]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 178418858HCID 178418858, compound

Product 1

HCID 178419025HCID 178419025, compoundYield 40.4%

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

Nitrogen (N2) gas was bubbled through a solution of 5-bromo-2-[2-(2-methyl-pyrrolidin-1-yl)-ethyl]-1H-benzoimidazole (0.19 g, 0.6 mmol) and 4-cyanophenylboronic acid (0.13 g, 0.9 mmol) in 1,2-dimethoxyethane (4 mL) and H2O (2 mL). To the mixture was added 2M Na2CO3 (1.2 mL, 2.4 mmol) and Pd(dppf)2Cl2:CH2Cl2 (1:1), and this mixture heated to 80° C. After approximately 24 h, the reaction mixture was cooled and extracted with ethyl acetate. The organic layer was then washed with H2O and distilled to dryness. The crude product was purified by column chromatography to afford the title compound (0.08 g). 1H NMR (400 MHz, CDCl3) δ 1.18 (d, 3H), 1.52-1.62 (m, 1H), 1.77-1.95 (m, 2H), 2.03-2.12 (m, 1H), 2.30 (q, 1H), 2.47-2.56 (m, 1H), 2.57-2.62 (m, 1H), 3.15-3.20 (m, 2H), 3.21-3.35 (m, 2H), 7.43 (dd, J=1.7 & 8.3, 1H), 7.62 (d, 1H), 7.68-7.73 (m, 4H), 7.76 (s, 1H); 13C NMR (400 MHz, CDCl3) δ 19.5, 22.2, 27.4, 33.2, 51.5, 53.3, 60.5, 109.9, 118.9, 121.2, 127.5, 132.2, 133.0, 146.1, 156.1 (2 peaks overlapping and some 13C peaks were not readily identified due to exchange broadening). APPI-MS: (M+1)+ at 331 m/z.

Workup

  1. temperaturethe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was then washed with H2O
  4. distillationdistilled to dryness
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-22d2e8d8597641aa8fb4fe533a4c1dde
Source dataset
uspto-grants-2008_04
Patent number
US07358263B2

Reaction notes

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