Ethanol → HCID 68857594, compound

HRID 1965975Notes

Reaction equation

HRID 1965975 reaction equation
Br[CH2:2][C:3]1[C:13]2[CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][C:4]=1[Cl:21].[N:22]1[CH:27]=[CH:26][CH:25]=[C:24](B(O)O)[CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1(C)C=CC=CC=1.O>[C:17]([O:16][C:14]([N:10]1[CH2:11][CH2:12][C:13]2[C:3]([CH2:2][C:24]3[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=3)=[C:4]([Cl:21])[CH:5]=[CH:6][C:7]=2[CH2:8][CH2:9]1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 59787403HCID 59787403, compound

Product 1

HCID 68857594HCID 68857594, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

Combine 6-bromomethyl-3-tert-butoxycarbonyl-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (700 mg, 1.89 mmol), pyridine-3-boronic acid (273 mg, 2.22 mmol), tetrakis(triphenylphospine)palladium(0) (1.1 g, 0.95 mmol), and sodium carbonate (600 mg, 5.66 mmol) in a mixture of toluene (14 mL), ethanol (3.5 mL) and water (0.7 mL). Heat the mixture to 60° C. for 12 h under nitrogen. Cool the reaction and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane and hexane/EtOAc (10:1, 5:1 and 1:1) to obtain 3-tert-butoxycarbonyl-7-chloro-6-pyridin-3-ylmethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine as an off-white solid (410 mg, 59%).

Workup

  1. temperatureCool
  2. customthe reaction
  3. concentrationconcentrate in vacuo
  4. customPurify by chromatography on silica gel eluting with hexane and hexane/EtOAc (10:1, 5:1 and 1:1)

Sources & evidence

ORD record
ord-463275e6556441d39dc12e147d647779
Source dataset
uspto-grants-2013_04
Patent number
US08420631B2

Reaction notes

Loading…