Ammonium Chloride → HCID 178431104, compound

HRID 389444Notes

Reaction equation

[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[CH:19]=[C:18](I)[CH:17]=[N:16]2)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([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:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[CH:19]=[C:18]([B:28]3[O:32][C:31]([CH3:34])([CH3:33])[C:30]([CH3:36])([CH3:35])[O:29]3)[CH:17]=[N:16]2)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred solution of 1-(trans-4-{[tert-butyl(dimethyl)silyl]-oxy}cyclohexyl)-4-iodo-1H-pyrazole (1.14 g, 2.80 mmol) in THF (30.0 mL) was cooled to 0° C. and treated with isopropylmagnesium chloride (2.0 M in THF, 2.31 mL, 4.63 mmol), added dropwise under an atmosphere of nitrogen over 5 min. The reaction mixture was stirred at 0° C. for another 1 h, then treated 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.95 mL, 5.6 mmol) and stirred at RT for another hour. The mixture was treated with saturated aqueous NH4Cl (10 mL) and extracted with EtOAc (3×20 mL). The extracts were washed with water (10 mL), brine (15 mL), and dried over Na2SO4. Solvent was removed under reduced pressure to give a residue which was purified by flash chromatography (10% EtOAc:hexane) to provide 1.10 g (96%) of the title compound. MS (ESI): 405.95 [M+H]+; HPLC tR=3.21 min.

Workup

additionadded dropwise under an atmosphere of nitrogen over 5 min
extractionextracted with EtOAc (3×20 mL)
washThe extracts were washed with water (10 mL), brine (15 mL)
dry with materialdried over Na2SO4
customSolvent was removed under reduced pressure
customto give a residue which
customwas purified by flash chromatography (10% EtOAc:hexane)

Sources & evidence

ORD record: ord-308912143a1145cb9621158ed2c4de0b
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08378104B2

Reaction notes

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