Ammonium Chloride → HCID 178431104, compound

HRID 511336Notes

Reaction equation

HRID 511336 reaction equation
[C:1]([Si:5]([CH3:20])([CH3:19])[O:6][CH:7]1[CH2:12][CH2:11][CH:10]([N:13]2[CH:17]=[C:16](I)[CH:15]=[N:14]2)[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].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-]>C1COCC1>[Si:5]([O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[CH:17]=[C:16]([B:28]3[O:32][C:31]([CH3:34])([CH3:33])[C:30]([CH3:36])([CH3:35])[O:29]3)[CH:15]=[N:14]2)[CH2:9][CH2:8]1)([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 109757592-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 667595941H-Pyrazole, 1-[trans-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]cyclohexyl]-4-iodo-2×HCID 178418918HCID 178418918, compound

Product 1

HCID 178431104HCID 178431104, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred THF (30.00 mL) solution of 1-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-4-iodo-1H-pyrazole (Compound 137B, 1.1400 g, 2.8053 mmol) was added 2.00 M of isopropylmagnesium chloride in THF (2.31 mL, 4.63 mmol) dropwise under an atmosphere of Nitrogen in 5 min at 0° C. The reaction mixture was stirred at 0° C. for another hour. 2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.9577 mL, 5.610 mmol) was added at 0° C. and then the mixture was stirred at room temparature for another hour. The mixture was treated with saturated NH4Cl (10 ml), extracted with EtOAc (20 ml×3). The extracts were washed with water (10 ml), brine (15 ml), dried over Na2SO4. Solvent was removed under reduced pressure to give a residue which was purified by flash chromatography (10% EtOAc/hexane). MS (ES+): m/z=407.18 [MH+]. HPLC: tR=3.21 min (polar—5 min, ZQ3).

Workup

  1. stirringthe mixture was stirred at room temparature for another hour
  2. extractionextracted with EtOAc (20 ml×3)
  3. washThe extracts were washed with water (10 ml), brine (15 ml)
  4. dry with materialdried over Na2SO4
  5. customSolvent was removed under reduced pressure
  6. customto give a residue which
  7. customwas purified by flash chromatography (10% EtOAc/hexane)
  8. customHPLC: tR=3.21 min (polar—5 min, ZQ3)

Sources & evidence

ORD record
ord-440523b3345c4b979019d8e93c8badef
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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