Tetrahydrofuran → HCID 67003946, compound

HRID 2095636Notes

Reaction equation

HRID 2095636 reaction equation
I[C:2]1[C:3]([CH3:12])=[N:4][N:5]([CH2:7][C@H:8]([OH:11])[CH2:9][OH:10])[CH:6]=1.IC1C=NN(C[C@H](O)CO)C=1C.C1COCC1.C([Mg]Cl)(C)C.CO[B:37]1[O:41][C:40]([CH3:43])([CH3:42])[C:39]([CH3:45])([CH3:44])[O:38]1.[NH4+].[Cl-]>>[CH3:12][C:3]1[C:2]([B:37]2[O:41][C:40]([CH3:43])([CH3:42])[C:39]([CH3:45])([CH3:44])[O:38]2)=[CH:6][N:5]([CH2:7][C@H:8]([OH:11])[CH2:9][OH:10])[N:4]=1

Participants

7

Reactant 6

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 109757592-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 67004488HCID 67004488, compoundHCID 67004883HCID 67004883, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 67003946HCID 67003946, compound

Procedure

To a solution of (S)-3-(4-iodo-3-methylpyrazol-1-yl)-propane-1,2-diol (20.0 mg, 0.0709 mmol) and (S)-3-(4-Iodo-5-methylpyrazol-1-yl)-propane-1,2-diol (20.0 mg, 0.0709 mmol) in THF (1 mL, 10 mmol) was added 2 M isopropylmagnesium chloride in THF (0.18 mL, 0.36 mmol) at 0° C., and the reaction was allowed to warm to rt over 30 min. 2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.070 mL, 0.43 mmol) was then added, and the mixture was stirred at rt 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 concentrated in vacuo to afford the title compound as a clear oil. It was used in the Suzuki coupling without further purification.

Workup

  1. customto quench
  2. customthe organic solvent was removed in vacuo
  3. extractionThe material was extracted with DCM and water
  4. concentrationthe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-239477e3954d43ba8cc009a0719c61b5
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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