Azidotrimethylsilane → HCID 178519389, compound

HRID 2249523Notes

Reaction equation

HRID 2249523 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]#[C:10][C:11]1[CH:12]=[C:13]([C:23]([N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:24])[N:14](C(OC(C)(C)C)=O)[CH:15]=1.C[Si]([N:34]=[N+:35]=[N-:36])(C)C>>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[NH:36][N:35]=[N:34][C:10]=1[C:11]1[CH:12]=[C:13]([C:23]([N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:24])[NH:14][CH:15]=1

Participants

3

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 59639696HCID 59639696, compound

Product 1

HCID 178519389HCID 178519389, compoundYield 11%

Conditions

Temperature
150 °C

Procedure

(4-(2-(2,3-difluorophenyl)ethynyl)-1-BOC-pyrrol-2-yl)(pyrrolidin-1-yl)methanone (0.2 g, 0.5 mmol) was dissolved in trimethylsilylazide (3 mL) and heated at 150° C. for 18 hr. The solvent was evaporated and the crude product was purified by Biotage HPFC system (100% EtOAC) to afford title compound as a brown foam (0.019 g, 11%).; Mass Spec FIA MS 344; 1H NMR(CDCl3, 500 MHz) 10.05(s,1H), 7.06-7.25(m, 3H), 6.98(s,1H), 6.71(s,1H),3.55-3.60(m,4H), 1.79-1.95(m,4H).

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was purified by Biotage HPFC system (100% EtOAC)

Sources & evidence

ORD record
ord-74cf3a2d133442e0b738329366b9c6dc
Source dataset
uspto-grants-2008_01
Patent number
US07314885B2

Reaction notes

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