Azido(trimethyl)stannane → HCID 178477842, compound

HRID 1506852Notes

Reaction equation

HRID 1506852 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([C:11]#[N:12])[O:8][C:7]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[C:6]=2[CH:25]=1.C[Sn]([N:30]=[N+:31]=[N-:32])(C)C>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([C:11]3[NH:32][N:31]=[N:30][N:12]=3)[O:8][C:7]([CH:19]3[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]3)([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[C:6]=2[CH:25]=1

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 89907420HCID 89907420, compound

Product 1

HCID 178477842HCID 178477842, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

500 mg 6-chloro-4,4-dicyclohexyl-4H-benzo[1,3]dioxine-2-carbonitrile and 572 mg trimethyltin azide were dissolved in 23 ml xylene. The reaction mixture was refluxed for 4 hours. Then the solvent was removed in vacuo and the crude product purified by preparative HPLC (C18 reverse phase column, elution with water/MeCN gradient with 0.1% TFA). The fractions containing the product were evaporated and lyophilized to yield a solid which was washed three times with heptanes to remove traces of tin by-product. Yield: 238 mg.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. customThen the solvent was removed in vacuo
  3. customthe crude product purified by preparative HPLC (
  4. washC18 reverse phase column, elution with water/MeCN gradient with 0.1% TFA)
  5. additionThe fractions containing the product
  6. customwere evaporated
  7. customto yield a solid which
  8. washwas washed three times with heptanes
  9. customto remove traces of tin by-product

Sources & evidence

ORD record
ord-9bf51a29c198495e92603f42d1321039
Source dataset
uspto-grants-2015_12
Patent number
US09221784B2

Reaction notes

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