Water → 3-Methylthieno[3,2-b]pyridine

HRID 226062Notes

Reaction equation

HRID 226062 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
130 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-091a537c5ae44241a60172eedb0b6e62
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

Loading…