Boron tribromide → HCID 136337204, 화합물

HRID 1891206노트

반응식

HRID 1891206 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:28]C)=[C:6]([C:8]2[N:13]=[C:12]([N:14]3[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:16]=[N:15]3)[CH:11]=[CH:10][CH:9]=2)[CH:7]=1.B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:28])=[C:6]([C:8]2[N:13]=[C:12]([N:14]3[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:16]=[N:15]3)[CH:11]=[CH:10][CH:9]=2)[CH:7]=1

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 68489227HCID 68489227, 화합물

생성물 1

HCID 136337204HCID 136337204, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a cooled (0° C.) solution of the title compound from Example 2 Step A (2.89 g, 7.06 mmol) in DCM (30 mL) was added dropwise BBr3 (21.2 mL, 1.0 M in DCM, 21.2 mmol). After addition was complete, the cooling bath was removed, and the reaction mixture was allowed to stir at room temperature. After 1.5 h, the mixture was cooled to 0° C., then was quenched by careful addition (exothermic, gas evolution) of sat aq NaHCO3 (100 mL). The resulting mixture was diluted with DCM, the phases were separated, and the organic phase was concentrated in vacuo. Purification by chromatography on silica gel (0 to 35% EtOAc in hexanes, then 35 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 395.8 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 11.79 (s, 1H), 8.18 (s, 1H), 8.10 (t, J=8.0 Hz, 1H), 7.95 (d, J=8.0 Hz, 1H), 7.54 (d, J=8.0 Hz, 1H), 7.49 (dd, J=10.0, 3.0 Hz, 1H), 7.09-7.06 (m, 1H), 6.98 (dd, J=9.0, 5.0 Hz, 1H), 4.39 (q, J=7.0 Hz, 2H), 1.39 (t, J=7.0 Hz, 3H).

후처리

  1. additionAfter addition
  2. customthe cooling bath was removed
  3. temperaturethe mixture was cooled to 0° C.
  4. customwas quenched by careful addition (exothermic, gas evolution) of sat aq NaHCO3 (100 mL)
  5. additionThe resulting mixture was diluted with DCM
  6. customthe phases were separated
  7. concentrationthe organic phase was concentrated in vacuo
  8. customPurification by chromatography on silica gel (0 to 35% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-372f2f57d6794340a0a0f8c610b0c268
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507512B2

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