Water → Ammonia

HRID 1639665Notes

Reaction equation

HRID 1639665 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.C([O-])([O-])=O.[Na+].[Na+].O>COCCOC.O.CCO.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>[NH3:7].[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

9

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 139377Methylboronic AcidHCID 132204283-Bromothieno[3,2-b]pyridine

Product 2

HCID 222AmmoniaHCID 577526103-Methylthieno[3,2-b]pyridine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
130 °C

Procedure

Prepare three microwavable reaction vials containing 3-bromo-thieno[3,2-b]pyridine (214 mg, 1.0 mmol) and methylboronic acid (180 mg, 3.0 mmol) in DME/water/EtOH=7/3/1 (4 mL). Add 2 M Na2CO3 (1.5 mL, 3.0 mmol) and bubble in nitrogen gas for 15 min. Add Pd(PPh3)4 (58 mg, 0.05 mmol) and seal the vials. Heat the vials at 130° C. for 30 min in the microwave. Combine all the reaction mixtures, add water and CH2Cl2 and extract. Separate the CH2Cl2 layer, dry over Na2SO4, filter, and evaporate. Purify the resulting material using silica gel chromatography, eluting with hexane:ethyl acetate: 2 M NH3 in MeOH=20:4:1, to give the title compound (193 mg, 43%. ES/MS m/z 150 (M+1)+.

Workup

  1. customPrepare
  2. customthree microwavable reaction vials
  3. custombubble in nitrogen gas for 15 min
  4. customthe reaction mixtures
  5. extractionextract
  6. customSeparate the CH2Cl2 layer
  7. dry with materialdry over Na2SO4
  8. filtrationfilter
  9. customevaporate
  10. customPurify the resulting material
  11. washeluting with hexane

Sources & evidence

ORD record
ord-2bbdeafbdecc4e31a52dfede676e2e00
Source dataset
uspto-grants-2012_02
Patent number
US08110580B2

Reaction notes

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