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Ammonium Chloride → 1-(3-Benzyloxy-2,2-difluoropropyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

HRID 2279881
Notes
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Reaction equation

HRID 2279881 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([F:19])([F:18])[CH2:11][N:12]1[CH:16]=[C:15](I)[CH:14]=[N:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.CO[B:27]1[O:31][C:30]([CH3:33])([CH3:32])[C:29]([CH3:35])([CH3:34])[O:28]1.[Cl-].[NH4+]>C1COCC1>[CH2:1]([O:8][CH2:9][C:10]([F:19])([F:18])[CH2:11][N:12]1[CH:16]=[C:15]([B:27]2[O:31][C:30]([CH3:33])([CH3:32])[C:29]([CH3:35])([CH3:34])[O:28]2)[CH:14]=[N:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 109757592-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 678137681-(3-benzyloxy-2,2-difluoropropyl)-4-iodo-1H-pyrazole2×HCID 178418918HCID 178418918, compound

Product 1

HCID 678139791-(3-Benzyloxy-2,2-difluoropropyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleYield 736.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

A solution of 1-(3-benzyloxy-2,2-difluoropropyl)-4-iodo-1H-pyrazole (Compound 59F, 1.8 g, 4.7 mmol) in THF (40 mL) was cooled to −78° C., treated with iPrMgCl (4.75 mL, 9.5 mmol, 2M) and the temperature was raised to −40° C. After 20 min stirring at −40° C., reaction mixture was cooled to −78° C. and treated with 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.091 mL, 0.56 mmol). The reaction mixture was allowed to warm to RT, treated with sat. aq. ammonium chloride (20 mL) and extracted with ethyl acetate (20 mL). The organic layer was dried over Na2SO4, filtered and concentrated to give 1.56 g (89%) of desired product as an oil. 1H NMR (500 MHz, CDCl3) δ 7.81 (s, 1H), 7.78 (s, 1H), 7.36-7.33 (m, 5H), 4.64-4.59 (m, 4H), 3.56 (t, J=12 Hz, 2H), 1.26 (s, 12H).

Workup

  1. customreaction mixture
  2. temperaturewas cooled to −78° C.
  3. temperatureto warm to RT
  4. extractionextracted with ethyl acetate (20 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e3e06df473414f14aed961aedc9c9837
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09133224B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes