tert-Butanol → HCID 66576768、化合物

HRID 1521606ノート

反応式

HRID 1521606 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:12]=[N:13][N:14]=[C:7]1[CH2:6][CH2:5]2.[CH3:15][O:16][C:17]([C:19]1([C:22]2[CH:23]=[C:24](B(O)O)[CH:25]=[N:26][CH:27]=2)[CH2:21][CH2:20]1)=[O:18].C(=O)([O-])[O-].[K+].[K+].C(O)(C)(C)C>CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl.O>[CH:12]1[N:8]2[C:9]3[C:4]([CH2:5][CH2:6][C:7]2=[N:14][N:13]=1)=[CH:3][C:2]([C:24]1[CH:23]=[C:22]([C:19]2([C:17]([O:16][CH3:15])=[O:18])[CH2:20][CH2:21]2)[CH:27]=[N:26][CH:25]=1)=[CH:11][CH:10]=3

参加物

7

反応物 4

HCID 6386tert-ButanolHCID 11430Potassium CarbonateHCID 21543699HCID 21543699、化合物HCID 70977491HCID 70977491、化合物

生成物 1

HCID 66576768HCID 66576768、化合物

試薬・触媒・溶媒 2

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)触媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

To a vial containing the title compound from Example 22 Step B (0.12 g, 0.48 mmol), the title compound from Example 71 Step C (0.13 g, 0.59 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (6.8 mg, 9.6 μmol), and potassium carbonate (0.200 g, 1.44 mmol) were added tert-butanol (5.3 mL) and water (0.67 mL). The vial was flushed with nitrogen, sealed tightly and heated to 80° C. overnight. The reaction solution was then cooled to room temperature and concentrated under reduced pressure. The resulting material was diluted with acetonitrile and purified by HPLC (C18 column, 10 to 100% acetonitrile/water, both 0.1% v/v trifluoroacetic acid). Fractions containing product were combined, aqueous 1 N HCl solution was added, and the resulting solution concentrated under reduced pressure to provide the title compound: LCMS m/z 347.00 [M+H]+; 1H NMR (500 MHz, CD3OD) δ 10.1 (s, 1H), 9.21 (s, 1H), 9.02 (s, 1H), 8.99 (s, 1H), 8.12-8.03 (m, 3H), 3.70 (s, 3H), 3.51-3.48 (m, 2H), 3.41-3.38 (m, 2H), 1.85-1.82 (m, 2H), 1.59-1.56 (m, 2H).

後処理

  1. customThe vial was flushed with nitrogen
  2. customsealed tightly
  3. temperatureThe reaction solution was then cooled to room temperature
  4. concentrationconcentrated under reduced pressure
  5. additionThe resulting material was diluted with acetonitrile
  6. custompurified by HPLC (C18 column, 10 to 100% acetonitrile/water
  7. additionFractions containing product
  8. additionaqueous 1 N HCl solution was added
  9. concentrationthe resulting solution concentrated under reduced pressure

出典と根拠

ORDレコード
ord-dd5144ba9fa54717bdec66f201fb892c
出典データセット
uspto-grants-2015_07
特許番号
US09073929B2

反応ノート

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