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

2-(Tributylstannyl)pyridine → 10,11-Dihydro-10-[4-(2-pyridinyl)benzoyl]-5H-pyrrolo[2,1-c][1,4]benzodiazepine

HRID 440774
Notes
Print preview

Reaction equation

HRID 440774 reaction equation
I[C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]3[CH:19]=[CH:20][CH:21]=[C:10]3[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)CCC>C1(C)C=CC=CC=1.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>[N:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]3[CH:19]=[CH:20][CH:21]=[C:10]3[CH2:9]2)=[O:7])=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 15298021HCID 15298021, compound

Product 1

HCID 2240533010,11-Dihydro-10-[4-(2-pyridinyl)benzoyl]-5H-pyrrolo[2,1-c][1,4]benzodiazepineYield 81.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 1140
Toluene
Solvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2.0 g of 10,11-dihydro-10-(4-iodobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine and 4.39 g of 2-[(tri-n-butyl)stannyl]pyridine in 30 ml of toluene under nitrogen is added 0.2 g of tetrakis(triphenylphosphine)palladium and the mixture heated to 120° C. for 16 hours. The toluene is evaporated in vacuo and the oily residue diluted with 50 ml of chloroform and washed with water, dried (Na2SO4), filtered through diatomaceous earth and evaporated in vacuo to give a residue which is columned on silica gel by elution with 7:1 to 1:1 ethyl acetate:hexane to give 1.44 g of the desired product as a solid, m.p. 170°-172° C.; M+H=366.1; M+Na=388.1.

Workup

  1. customThe toluene is evaporated in vacuo
  2. additionthe oily residue diluted with 50 ml of chloroform
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered through diatomaceous earth
  6. customevaporated in vacuo
  7. customto give a residue which
  8. washis columned on silica gel by elution with 7:1 to 1:1 ethyl acetate

Sources & evidence

ORD record
ord-0af347db7cd14409b399f7dbd23d2965
Source dataset
uspto-grants-1996_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05521173

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes