Dichloromethane → HCID 24949073, compound

HRID 877418Notes

Reaction equation

HRID 877418 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]2[NH:19][C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[N:17][N:16]=2)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:26](Cl)Cl.[Si](C=[N+]=[N-])(C)(C)C>CO>[CH3:26][N:19]1[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[N:17][N:16]=[C:15]1[C:13](=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 167693TrimethylsilyldiazomethaneHCID 178520584HCID 178520584, compound

Product 1

HCID 24949073HCID 24949073, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A sample of 14b (3.0 mg, 0.009 mmol) was dissolved in a mixture of MeOH (0.1 mL): CH2Cl2 (0.1 mL). TMSCHN2 (7 μL, 0.013 mmol) was added dropwise causing gas to evolve, and after 0.5 h the reaction mixture was quenched with the dropwise addition of AcOH (50 μL). All volatiles were removed under reduced pressure to afford a residue that was purified by preparative thin layer chromatography (SiO2, 50% EtOAc-hexanes). The title compound (0.735 mg, 23%) was isolated along with the two other regioisomers (16; 1.01 mg, 32%; 17; 0.496 mg, 16%) as a colorless solid: 1H NMR (CDCl3, 500 MHz) δ 8.71 (dd, 1H, J=0.9, 4.9 Hz), 8.33 (d, 1H, J=8.0 Hz), 7.88 (dt, 1H, J=1.8, 7.8 Hz), 7.41 (ddd, 1H, J=1.1, 4.9, 7.6 Hz), 7.28 (m, 2H), 7.16 (m, 3H), 4.37 (s, 3H), 3.28 (t, 2H, J=7.4 Hz), 2.61 (t, 2H, J=7.7 Hz), 1.78 (m, 2H), 1.64 (m, 2H), 1.42 (m, 4H); HRMS-ESI-TOF m/z 349.2020 ([M+H]+, C21H24N4O requires 349.2023). Tetrazoles (15a-15e, 19a, 19b):

Workup

  1. customafter 0.5 h the reaction mixture was quenched with the dropwise addition of AcOH (50 μL)
  2. customAll volatiles were removed under reduced pressure
  3. customto afford a residue that
  4. customwas purified by preparative thin layer chromatography (SiO2, 50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-69b46e5a0fea40189ec1ccebea1ec003
Source dataset
uspto-grants-2015_03
Patent number
US08987312B2

Reaction notes

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