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

HRID 1956343
Notes
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Reaction equation

HRID 1956343 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, dried(Na2SO4)
  4. filtrationfiltered through diatomaceous earth
  5. customevaporated in vacuo
  6. customto give a residue which
  7. washis columned on silica gel by elution with 7:1 to 1:1 ethyl acetate

Sources & evidence

ORD record
ord-72fc42a5ae0341718aff7c12cc059f96
Source dataset
uspto-grants-1998_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05780471

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes