Azido(trimethyl)stannane → HCID 178420043, compound

HRID 1866864Notes

Reaction equation

HRID 1866864 reaction equation
[N:1]([Sn](C)(C)C)=[N+:2]=[N-:3].[C:8]1([C:14]2([C:21]3[CH:28]=[C:27]([O:29][CH2:30][C:31]4[CH:40]=[CH:39][C:38]5[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=5)[N:32]=4)[CH:26]=[CH:25][C:22]=3[C:23]#[N:24])[CH2:19][CH:18]3[CH2:20][CH:15]2[CH2:16][CH2:17]3)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1(C)C=CC=CC=1>[C:8]1([C:14]2([C:21]3[CH:28]=[C:27]([CH:26]=[CH:25][C:22]=3[C:23]3[NH:24][N:3]=[N:2][N:1]=3)[O:29][CH2:30][C:31]3[CH:40]=[CH:39][C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[N:32]=3)[CH2:19][CH:18]3[CH2:20][CH:15]2[CH2:16][CH2:17]3)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 57978644HCID 57978644, compound

Product 1

HCID 178420043HCID 178420043, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

Azidotrimethyltin (82.0 mg, 0.40 mmol) was added to a stirred solution of 6a (40.0 mg, 0.09 mmol) in toluene (0.6 mL) at room temperature and the resulting mixture heated to 140° C. After 72 h, the reaction mixture was cooled to room temperature, and the volatiles were removed in vacuo. The residue was taken up in cold hydrogen chloride/MeOH (1 mL; saturated solution) and stirred for 20 min at room temperature. The reaction mixture was concentrated in vacuo, and the crude residue was purified by flash chromatography on silica gel (gradient elution, 0-10% methanol/methylene chloride as eluent) to furnish the title compound as an off-white foam. Rf: 0.15 (1:2 hexane:EtOAc). m/z (ES) 474 (MH)+. 1H NMR (500 M, CDCl3): δ 0.89-0.93 (m, 1H), 1.19-1.26 (m, 1H), 1.26-1.40 (m, 2H), 1.46-1.55 (m, 1H), 1.72 (br d, 1H), 1.88 (td, J=2.8, 13.6 Hz, 1H), 2.03 (dd, J=2.3, 13.7 Hz, 1H), 2.34 (br s, 1H), 3.01 (br d, J=3.6 Hz, 1H), 5.55 (s, 2H), 6.94 (dd, J=2.3, 8.4 Hz, 1H), 7.0-7.22 (m, 3H), 7.22-7.32 (m, 3H), 7.62-7.68 (m, 2H), 7.78-7.86 (m, 2H), 7.90-7.96 (m, 1H), 8.20 (m, 1H), 8.37 (m, 1H).

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. customthe volatiles were removed in vacuo
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe crude residue was purified by flash chromatography on silica gel (gradient elution, 0-10% methanol/methylene chloride as eluent)

Sources & evidence

ORD record
ord-eec1ab52f9f74d3183166fee1c5e3e2f
Source dataset
uspto-grants-2009_12
Patent number
US07629467B2

Reaction notes

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