Tri-o-tolylphosphine → 5'-(2-Furyl)spiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine]

HRID 48519Notes

Reaction equation

HRID 48519 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH2:10][C:9]3([CH:15]4[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]4)[CH2:11]3)[O:8][C:5]2=[N:6][CH:7]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[Cl-].[Li+].C([Sn](CCCC)(CCCC)[C:47]1[O:48][CH:49]=[CH:50][CH:51]=1)CCC>COCCOC.C(Cl)(Cl)Cl.CO>[O:48]1[CH:49]=[CH:50][CH:51]=[C:47]1[C:2]1[CH:3]=[C:4]2[CH2:10][C:9]3([CH:15]4[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]4)[CH2:11]3)[O:8][C:5]2=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 80271Tri-o-tolylphosphineHCID 433294Lithium ChlorideHCID 43936882-(Tributylstannyl)furanHCID 103571335'-bromospiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine]

Product 1

HCID 159082405'-(2-Furyl)spiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine]Yield 89.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution containing 5′-bromospiro[1-azabicyclo[2.2.2] octane-3,2′(3′H)-furo[2,3-b]pyridine] (103.5 mg, 0.351 mmol), tris(dibenzylidineacetone)dipalladium (0) (14 mg, 0.015 mmol), tri(o-tolyl)phosphine (44.4 mg, 0.146 mmol), lithium chloride (62 mg, 1.46 mmol), and 2-(tri-n-butylstannyl)furan (0.17 g, 0.476 mmol) in 1,2-dimethoxyethane (1 ml) was heated under reflux for 2 h. The solution was evaporated, and the residue was taken up in chloroform and filtered. The filtrate was evaporated then purified by HPLC using a gradient of 0-25% 1:1:2 7M methanolic ammonia:methanol:chloroform and chloroform to obtain the title compound (89 mg, 0.313 mmol, 89%) as a pale solid: electrospray MS (m/z, relative intensity) 283 ([MH]+, 100).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. customThe solution was evaporated
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. customthen purified by HPLC

Sources & evidence

ORD record
ord-8032d277f4844aaebe6dc4c4b1cb01e7
Source dataset
uspto-grants-2004_03
Patent number
US06703502B2

Reaction notes

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