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2-(Tri-n-butylstannyl)thiophene → 9-tert-butyl-2-fluoro-3-methoxy-14-(thiophen-2-yl)-5,6,10,11,12,13-hexahydroazocino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8(9H)-one

HRID 1971761
Notes
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Reaction equation

HRID 1971761 reaction equation
Br[C:2]1[C:3]2[CH2:23][CH2:22][CH2:21][CH2:20][N:19]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:18](=[O:28])[C:4]=2[N:5]2[CH2:14][CH2:13][C:12]3[CH:11]=[C:10]([O:15][CH3:16])[C:9]([F:17])=[CH:8][C:7]=3[C:6]=12.C([Sn](CCCC)(CCCC)[C:34]1[S:35][CH:36]=[CH:37][CH:38]=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>[C:24]([N:19]1[CH2:20][CH2:21][CH2:22][CH2:23][C:3]2[C:2]([C:34]3[S:35][CH:36]=[CH:37][CH:38]=3)=[C:6]3[C:7]4[CH:8]=[C:9]([F:17])[C:10]([O:15][CH3:16])=[CH:11][C:12]=4[CH2:13][CH2:14][N:5]3[C:4]=2[C:18]1=[O:28])([CH3:27])([CH3:26])[CH3:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 5812491714-bromo-9-tert-butyl-2-fluoro-3-methoxy-5,6,10,11,12,13-hexahydroazocino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8(9H)-one

Product 1

HCID 509388539-tert-butyl-2-fluoro-3-methoxy-14-(thiophen-2-yl)-5,6,10,11,12,13-hexahydroazocino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8(9H)-oneYield 75.5%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 1140TolueneSolvent

Procedure

To a degassed solution of 50 mg 27b and 62.3 mg 2-(tributylstannyl)thiophene in 3 mL toluene was added 12.9 mg tetrakis(triphenylphosphine)palladium(0). The mixture was stirred at reflux for 16 h. The crude reaction mixture purified by column chromatography over silica and was then triturated with diisopropyl ethyl ether/pentane (1:1) to give 38 mg 27c as a yellow solid.

Workup

  1. temperatureat reflux for 16 h
  2. customThe crude reaction mixture
  3. custompurified by column chromatography over silica
  4. customwas then triturated with diisopropyl ethyl ether/pentane (1:1)

Sources & evidence

ORD record
ord-bfe7ab11607740eca50fdf39b8b05d61
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08431564B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes