Water → 3-Methylthieno[3,2-b]pyridine

HRID 226062ノート

反応式

HRID 226062 の反応式
Br[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[S:4][CH:3]=1.[CH3:11]B(O)O.COCCOC.O.CCO.O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)Cl>[CH3:11][C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[S:4][CH:3]=1

参加物

7

反応物 4

HCID 962WaterHCID 139377Methylboronic AcidHCID 132204283-Bromothieno[3,2-b]pyridineHCID 86587095Dimethoxyethane ethanol water

生成物 1

HCID 577526103-Methylthieno[3,2-b]pyridine収率 129.3%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6344Dichloromethane溶媒

反応条件

温度
130 °C

実験手順

3 reaction vials are prepared: 214 mg of 3-bromo-thieno[3,2-b]pyridine (1.0 mmol) and 180 mg of methylboronic acid (3.0 mmol) are put in the each vial with 4 ml of DME/water/EtOH=7/3/1. 1.5 ml of 2 M Na2CO aq. (3.0 mmol) is added and N2 gas is bubbled in for 15 min. 58 mg of Pd(PPh3)4 (0.05 mmol) is added and each vials are sealed. These vials are heated at 130° C. for 30 min in the microwave. All reaction mixtures are combined, and water and CH2Cl2 are added. The CH2Cl2 layer are separated and dried over Na2SO4 and evaporated. The crude products are applied onto a silica-gel chromatography column (Hexane: AcOEt: 2 M NH3 in MeOH=20:4:1) to give 193 mg of the title compound. Yield 43%. mass spectrum (m/e): 150 (M+1); 1H-NMR (CDCl3): 8.76 (dd, 1H, J=4.7 Hz, 1.5 Hz), 8.20 (dd, 1H, J=8.2 Hz, 1.5 Hz), 7.43 (d, 1H, J=1.2 Hz), 7.29 (dd, 1H, J=8.2 Hz, 4.7 Hz), 2.58 (d, 3H, J=1.2 Hz) ppm.

後処理

  1. custom3 reaction vials
  2. customare prepared
  3. customN2 gas is bubbled in for 15 min
  4. customeach vials are sealed
  5. customAll reaction mixtures
  6. customThe CH2Cl2 layer are separated
  7. dry with materialdried over Na2SO4
  8. customevaporated

出典と根拠

ORDレコード
ord-091a537c5ae44241a60172eedb0b6e62
出典データセット
uspto-grants-2009_07
特許番号
US07557103B2

反応ノート

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