Tributylstannane → HCID 86725327, compound

HRID 925213Notes

Reaction equation

HRID 925213 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:28][CH2:27][C:10]2[C:11]3[C:12](Br)([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[C:13]([F:19])([F:18])[CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2].C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([N:6]1[CH2:28][CH2:27][C:10]2[C:11]3[CH:12]([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[C:13]([F:18])([F:19])[CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 5948TributylstannaneHCID 86725325HCID 86725325, compound

Product 1

HCID 86725327HCID 86725327, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Into a 500 ml flask, the product from step (b) (15.2 mmol) dissolved in toluene (100 ml) was placed. The flask was purged with Ar, followed by the addition of tributyltin hydride (8.36 ml, 31.11 mmol). The reaction mixture was placed in a pre-heated (110° C.) oil bath and stirred for 20 minutes. The reaction mixture was cooled, quenched with saturated aqueous Na2CO3, and extracted with EtOAc (3×). The combined EtOAc extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo to give the crude product. Purification by silica-gel chromatography (gradient elution: 0 to 15% DCM w/20% MeOH, 1% NH4OH in DCM:) gave the sub-title compound as a yellow oil (3.7 g). 1H NMR (300 MHz, CDCl3) δ 8.54-8.52 (m, 1H); 8.37-8.33 (m, 1H); 7.23-7.21 (m, 2H); 7.15-7.09 (m, 2H); 4.67 (d, J=19.2, 1H); 4.14-4.08 (m, 2H); 3.69-3.60 (m, 1H); 3.53-3.48 (m, 2H); 3.42-3.34 (m, 2H); 3.21-3.10 (m, 1H); 2.92-2.87 (m, 2H); 2.65-2.58 (m, 1H); 2.52-2.44 (m, 1H); 1.32-1.20 (m, 3H); MS: ESI (positive): 373 (M+1).

Workup

  1. customThe flask was purged with Ar
  2. temperatureThe reaction mixture was cooled
  3. customquenched with saturated aqueous Na2CO3
  4. extractionextracted with EtOAc (3×)
  5. washThe combined EtOAc extracts were washed with brine
  6. dry with materialdried over Na2SO4, and solvent
  7. customevaporated in vacuo
  8. customto give the crude product
  9. customPurification
  10. washby silica-gel chromatography (gradient elution: 0 to 15% DCM w/20% MeOH, 1% NH4OH in DCM:)

Sources & evidence

ORD record
ord-e68bb243dfff477a982277e8efef8460
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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