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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
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HRID 2279881 반응식
[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
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참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 109757592-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 678137681-(3-benzyloxy-2,2-difluoropropyl)-4-iodo-1H-pyrazole2회HCID 178418918HCID 178418918, 화합물

생성물 1

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

시약·촉매·용매

1
HCID 8028Tetrahydrofuran용매

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온도
-40 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e3e06df473414f14aed961aedc9c9837
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09133224B2

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