Tributylstannane → HCID 44550495, compound

HRID 2238433Notes

Reaction equation

HRID 2238433 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[N:16]([CH2:24][CH:25]=[CH:26][Cl:27])[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20].CCCC[SnH](CCCC)CCCC.CC(N=NC(C#N)(C)C)(C#N)C>C1C=CC=CC=1>[Cl:27][CH2:26][CH:25]1[C:2]2[C:11]3[CH:10]=[C:9]([S:12]([CH3:15])(=[O:13])=[O:14])[CH:8]=[CH:7][C:6]=3[CH:5]=[CH:4][C:3]=2[N:16]([C:17]([O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[O:23])[CH2:24]1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 75066242HCID 75066242, compound

Product 1

HCID 44550495HCID 44550495, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 204 (1.60 g, 3.37 mmol) in dry benzene (30 mL) was treated with Bu3SnH (0.91 mL, 3.38 mmol) followed by AIBN (0.1 g, 0.6 mmol). The mixture was stirred under N2 at reflux for 2 h, then concentrated under reduced pressure. The residue was dissolved in EtOAc, and the solution was diluted with hexane and refrigerated. The resulting semisolid was chromatographed on silica gel, eluting with CH2Cl2/EtOAc (19:1), and the product was triturated with i-Pr2O/hexane to give tert-butyl 1-(chloromethyl)-8-(methylsulfonyl)-1,2-dihydro-3H-benzo[e]indole-3-carboxylate (205) (0.88 g, 66%) as an amorphous solid: 1H NMR [(CD3)2SO] δ 8.41 (d, J=1.6 Hz, 1H), 8.2 (v br, 1H), 8.17 (d, J=8.6 Hz, 1H), 8.03 (d, J=8.9. Hz. H), 7.80 (dd, J=8.6, 1.8 Hz, 1H), 4.42-4.33 (m, 1H), 4.21 (t, J=10.4 Hz, 1H), 4.12 (dd, J=11.6, 2.9 Hz, 1H), 4.07 (dd, J=11.2, 3.4 Hz, 1H). 3.89 (dd, J=11.2, 7.1 Hz; 1H), 3.33 (s, 3H), 1.55 (s, 9H). Anal. (C19H22ClNO4S.½i-Pr2O) C, H, N.

Workup

  1. temperatureat reflux for 2 h
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc
  4. additionthe solution was diluted with hexane
  5. customThe resulting semisolid was chromatographed on silica gel
  6. washeluting with CH2Cl2/EtOAc (19:1)
  7. customthe product was triturated with i-Pr2O/hexane

Sources & evidence

ORD record
ord-a881d47472dd4868943453d51a2dd448
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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