Tetrahydrofuran → 1-[[(4S)-2,2-Dimethyl-1,3-dioxolan-4-yl]methyl]-5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

HRID 2095701Notes

Reaction equation

HRID 2095701 reaction equation
[CH3:1][C:2]1([CH3:15])[O:6][C@@H:5]([CH2:7][N:8]2[C:12]([CH3:13])=[C:11](I)[CH:10]=[N:9]2)[CH2:4][O:3]1.C1COCC1.C([Mg]Cl)(C)C.CO[B:28]1[O:32][C:31]([CH3:34])([CH3:33])[C:30]([CH3:36])([CH3:35])[O:29]1.[NH4+].[Cl-]>>[CH3:1][C:2]1([CH3:15])[O:6][C@@H:5]([CH2:7][N:8]2[C:12]([CH3:13])=[C:11]([B:28]3[O:32][C:31]([CH3:34])([CH3:33])[C:30]([CH3:36])([CH3:35])[O:29]3)[CH:10]=[N:9]2)[CH2:4][O:3]1

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 109757592-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 670046211-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4-iodo-5-methyl-1H-pyrazoleHCID 178418918HCID 178418918, compound

Product 1

HCID 670045381-[[(4S)-2,2-Dimethyl-1,3-dioxolan-4-yl]methyl]-5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Procedure

To a solution of 1-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4-iodo-5-methyl-1H-pyrazole (55.0 mg, 0.171 mmol) in THF (1 mL, 20 mmol) at rt was added 1.3 M of isopropylmagnesium chloride in THF (0.53 mL, 0.68 mmol), and the mixture was stirred for 1 h. The reaction was quenched with 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.14 mL, 0.85 mmol) and allowed to stir at rt for 1 h. Sat. NH4Cl was added, and the organic solvent was removed in vacuo. The material was extracted with DCM and water. The organic layer was purified via column chromatography, eluting with 5-10% EtOAc/hexanes. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a white solid. MS (ES+): m/z=322.21/323.20/324.20 (50/100/50) [MH+]. HPLC: tR=1.49 min (polar—3 min, UPLC-ACQUITY).

Workup

  1. stirringto stir at rt for 1 h
  2. customthe organic solvent was removed in vacuo
  3. extractionThe material was extracted with DCM and water
  4. customThe organic layer was purified via column chromatography
  5. washeluting with 5-10% EtOAc/hexanes
  6. additionThe fractions containing the pure product
  7. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-505d71aa15fe4cc59be3cb791709559b
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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