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Stannanecarbonitrile, tributyl- → HCID 22609748, compound

HRID 1936762
Notes
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Reaction equation

HRID 1936762 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25](I)[CH:26]=4)[N:21]=[CH:20][N:19]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Sn]([C:42]#[N:43])(CCCC)CCCC)CCC>O1CCOCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([C:42]#[N:43])[CH:26]=4)[N:21]=[CH:20][N:19]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 200512Stannanecarbonitrile, tributyl-HCID 21952131(1-Benzyl-1H-indazol-5-yl)-(6-iodoquinazolin-4-yl)-amine

Product 1

HCID 22609748HCID 22609748, compoundYield 44.3%

Reagents, catalysts & solvents 3

HCID 10974057(Butane-1,4-diyl)bis(diphenylphosphane)--dichloropalladium (1/1)Catalyst
HCID 11979704
Tetrakis(triphenylphosphine)palladium
Catalyst
HCID 312751,4-DioxaneSolvent

Procedure

(1-Benzyl-1H-indazol-5-yl)-(6-iodoquinazolin-4-yl)-amine (3.58 g) in dioxane (30 ml) under N2 was treated with tributyltin cyanide (2.51 g) and catalytic quantities of 1.4-bis-(diphenylphosphino)-butane palladium (II) chloride and tetrakis (triphenylphosphine) palladium at reflux for 5 days. The mixture was absorbed onto silica and chromatographed to give the title compound (1.25 g); δH [2H6]DMSO 10.20(1H,s), 9.15(1H,s), 8.65(1H,s), 8.24(1H,s), 8.18(2H,m), 7.89(1H,s), 7.70(2H,m), 7.30(5H,m), 5.70(2H,s); m/z (M+1)+377.

Workup

  1. temperatureat reflux for 5 days
  2. customThe mixture was absorbed onto silica
  3. customchromatographed

Sources & evidence

ORD record
ord-129b52f4d14a4a82b774c7b13fe22d98
Source dataset
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06391874B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes