Dimethylformamide → HCID 178455356, compound

HRID 2095714Notes

Reaction equation

HRID 2095714 reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([N:15]2[CH:19]=[C:18]([I:20])[CH:17]=[N:16]2)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1C[O:24][CH2:23]C1.[Li+].CC([N-]C(C)C)C.C1CCCCC1.CN(C=O)C.[NH4+].[Cl-]>>[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[C:19]([CH:23]=[O:24])=[C:18]([I:20])[CH:17]=[N:16]2)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

7

Reactant 6

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 8078CyclohexaneHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 667595941H-Pyrazole, 1-[trans-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]cyclohexyl]-4-iodo-

Product 1

HCID 178455356HCID 178455356, compound

Procedure

A solution of 1-[4-(tert-butyl-dimethylsilanyloxy)-cyclohexyl]-4-iodo-1H-pyrazole (100.0 mg, 0.2461 mmol) in THF (6 mL, 70 mmol) was cooled to −78° C. and added 1.5 M of LDA in cyclohexane (0.213 mL, 0.320 mmol). After stirring for 5 min, DMF (0.1 mL, 1 mmol) was added slowly, and the mixture was stirred at −78° C. for 30 min. Sat. NH4Cl was added to quench, and the organic solvent was removed in vacuo. The material was extracted with DCM and water, and the organic layer was dry-loaded onto silica gel for column chromatography, eluting with 1-3% EtOAc/heptane. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a clear oil. MS (ES+): m/z=435.10 (100) [MH+]. HPLC: tR=2.18 min (polar—3 min, UPLC-ACQUITY).

Workup

  1. stirringthe mixture was stirred at −78° C. for 30 min
  2. customto quench
  3. customthe organic solvent was removed in vacuo
  4. extractionThe material was extracted with DCM and water
  5. washeluting with 1-3% EtOAc/heptane
  6. additionThe fractions containing the pure product
  7. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-5a49a8464dfe4514acc3c259f524a56f
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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