HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Water → 1,1-dimethylethyl 7-(3-{[(4-methyl-2-pyridinyl)methyl]oxy}-2-pyridinyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

HRID 63273
Notes
Print preview

Reaction equation

HRID 63273 reaction equation
Br[C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][N:11]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:25]2[CH:42]=[CH:41][C:28]3[CH2:29][CH2:30][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:32][CH2:33][C:27]=3[CH:26]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCOCC1.O.Cl[Pd]Cl.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.[Fe+2].C(OCC)(=O)C>[CH3:16][C:14]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:9][O:8][C:7]2[C:2]([C:25]3[CH:42]=[CH:41][C:28]4[CH2:29][CH2:30][N:31]([C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])[CH2:32][CH2:33][C:27]=4[CH:26]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)[CH:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 57505869tert-Butyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,4,5-tetrahydro-3H-benzo[d]azepine-3-carboxylateHCID 866705442-Bromo-3-{[(4-methyl-2-pyridinyl)methyl]oxy}pyridine

Product 1

HCID 706652431,1-dimethylethyl 7-(3-{[(4-methyl-2-pyridinyl)methyl]oxy}-2-pyridinyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Reagents, catalysts & solvents 4

HCID 24290Palladium ChlorideCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 8857Ethyl AcetateSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
120 °C

Procedure

To a degassed mixture of 2-bromo-3-{[(4-methyl-2-pyridinyl)methyl]oxy}pyridine (2.83 g), 1,1-dimethylethyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (4.54 g) and cesium carbonate (9.9 g) in dioxane:water (4:1, 40 ml) was added PdCl2.dppf (0.828 g). The reaction mixture was heated at 120° C. overnight. The reaction mixture was added to water and extraction was carried out with ethyl acetate. The organic layer was dried over sodium sulphate and the filtrate was concentrated in vacuo. The crude product was purified through silica, eluting with 0-40% ethyl acetate in hexane. Appropriate fractions were concentrated in vacuo to yield the title compound, 3.8 g (84%).

Workup

  1. dry with materialThe organic layer was dried over sodium sulphate
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe crude product was purified through silica
  4. washeluting with 0-40% ethyl acetate in hexane
  5. concentrationAppropriate fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-6b515ef1666142fa88156e73db3e63be
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09447074B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes