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

Allyltributylstannane → 2-Chloro-5,11-dihydro-11-ethyl-4-methyl-8-(2-propenyl)-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 2229323
Notes
Print preview

Reaction equation

HRID 2229323 reaction equation
Br[C:2]1[CH:21]=[N:20][C:5]2[N:6]([CH2:18][CH3:19])[C:7]3[N:15]=[C:14]([Cl:16])[CH:13]=[C:12]([CH3:17])[C:8]=3[NH:9][C:10](=[O:11])[C:4]=2[CH:3]=1.[CH2:22]([Sn](CCCC)(CCCC)CCCC)[CH:23]=[CH2:24]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:16][C:14]1[CH:13]=[C:12]([CH3:17])[C:8]2[NH:9][C:10](=[O:11])[C:4]3[CH:3]=[C:2]([CH2:24][CH:23]=[CH2:22])[CH:21]=[N:20][C:5]=3[N:6]([CH2:18][CH3:19])[C:7]=2[N:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 90628AllyltributylstannaneHCID 184666018-Bromo-2-chloro-5,11-dihydro-11-ethyl-4-methyl-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Product 1

HCID 184666152-Chloro-5,11-dihydro-11-ethyl-4-methyl-8-(2-propenyl)-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-oneYield 71.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compound
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 8-bromo-2-chloro-5,11-dihydro-11-ethyl-4-methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (12.6 g, 34.3 mmol) in DMF (25-0 mL) was degassed under reduced pressure for 20 min. Pd(PPh3)4 (775 mg, 0.7 mmol) was then added followed by allyltributyltin (12.5 mL, 41.1 mmol). After degassing under reduced pressure for 10 min, the mixture was heated to 100° C. for 7 h. The mixture was then concentrated under reduced pressure. The residue was purified by flash chromatography (hexane:EtOAc, 19:1) to give the title compound (8.04 g, 71% yield) as a yellow solid.

Workup

  1. customAfter degassing under reduced pressure for 10 min
  2. concentrationThe mixture was then concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography (hexane:EtOAc, 19:1)

Sources & evidence

ORD record
ord-ea34600dd94e4ccbbb35ca199c51fa6e
Source dataset
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06420359B1

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes