Boron tribromide → HCID 136337204、化合物

HRID 1891206ノート

反応式

HRID 1891206 の反応式
[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

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 68489227HCID 68489227、化合物

生成物 1

HCID 136337204HCID 136337204、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-372f2f57d6794340a0a0f8c610b0c268
出典データセット
uspto-grants-2013_08
特許番号
US08507512B2

反応ノート

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