Diisopropylethylamine → 5-(azidomethyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole

HRID 475174Notes

Reaction equation

HRID 475174 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH2:16]O)=[CH:15][C:10]=2[N:9]=[CH:8]1.C1(P([N:32]=[N+:33]=[N-:34])(C2C=CC=CC=2)=O)C=CC=CC=1.CCN(C(C)C)C(C)C>C1COCC1.C(Cl)Cl.O>[N:32]([CH2:16][C:14]1[CH:13]=[CH:12][C:11]2[N:7]([CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)[CH:8]=[N:9][C:10]=2[CH:15]=1)=[N+:33]=[N-:34]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 58325018(1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methanol

Product 1

HCID 712722435-(azidomethyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazoleYield 48.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 24 (2.2 g, 9.6 mmol) in THF (20 mL) under nitrogen at RT was added diphenylphosphoryl azide (3.96 g, 14.4 mmol) and DIPEA (5 mL). The reaction was stirred for 18 h then diluted with DCM (200 mL) and water (50 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (2:1) to afford 1.2 g (48%) of 5-(azidomethyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole (26) as yellow oil: MS (ESI) m/z=258.2 [M+1]+.

Workup

  1. dry with materialThe organic layer was dried (MgSO4)
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by SiO2 chromatography
  5. washeluting with petroleum ether/EtOAc (2:1)

Sources & evidence

ORD record
ord-5137989acf0644d383d2a0158b17c7c8
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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