Toluene → HCID 67287030, compound

HRID 1626420Notes

Reaction equation

HRID 1626420 reaction equation
Br[C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]2[CH:33]=[CH:32][C:14]([O:15][C:16]3[CH:25]=[C:24]4[C:19]([CH:20]([C:26]([O:28][CH3:29])=[O:27])[CH2:21][CH2:22][O:23]4)=[CH:18][C:17]=3[C:30]#[N:31])=[CH:13][CH:12]=2)=[O:10])[CH:5]=[CH:4][CH:3]=1.[CH3:34][C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][C:40]=1[CH3:41].C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>O>[C:30]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][C:16]=1[O:15][C:14]1[CH:32]=[CH:33][C:11]([C:9](=[O:10])[NH:8][C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([C:37]4[CH:38]=[CH:39][C:40]([CH3:41])=[C:35]([CH3:34])[CH:36]=4)[N:7]=3)=[CH:12][CH:13]=1)[O:23][CH2:22][CH2:21][CH:20]2[C:26]([O:28][CH3:29])=[O:27])#[N:31]

Participants

6

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27343483,4-Dimethylphenylboronic acidHCID 86664392HCID 86664392, compound

Product 1

HCID 67287030HCID 67287030, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 7-(4-(6-bromopyridin-2-ylcarbamoyl)phenoxy)-6-cyanochroman-4-carboxylate (51 mg, 0.1003 mmol), 3,4-dimethylphenylboronic acid (19.562 mg, 0.1304 mmol), sodium carbonate (31.901 mg, 0.301 mmol), toluene (1 mL), and water (0.1 mL) were placed in a vial with a Teflon lined screw cap. Argon was bubbled through the mixture for 10 minutes. Palladium (0) tetrakistriphenylphosphine (5.797 mg, 0.00501 mmol) was added and the vial was sealed. The vial was placed in a preheated sand bath (100° C.) and the mixture was stirred for 16 hours at that temperature. The mixture was cooled to ambient temperature and whole mixture was purified on silica gel (EtOAc-hexanes gradient) to provide 51.1 mg of the title compound as a thin film (95.5%).

Workup

  1. customcap
  2. customArgon was bubbled through the mixture for 10 minutes
  3. customthe vial was sealed
  4. customThe vial was placed in a preheated sand bath
  5. temperatureThe mixture was cooled to ambient temperature
  6. customwhole mixture was purified on silica gel (EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-e1d5a0dce82b41a7b7694cdbd030ff9b
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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