Dichloromethane → HCID 66760671, compound

HRID 389562Notes

Reaction equation

HRID 389562 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[S:4][C:3]=1[C:11]([NH2:13])=O.P(Cl)(Cl)(Cl)=O.C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl>C(#N)C>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[S:4][C:3]=1[C:11]#[N:13]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychloride2×HCID 66760607HCID 66760607, compound

Product 1

HCID 66760671HCID 66760671, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of 3-bromothieno[2,3-c]pyridine-2-carboxamide (750 mg, 2.92 mmol) in acetonitrile (20 mL) was added phosphorus oxychloride (816 μL, 8.75 mmol) and the mixture was heated under N2 for 1 hour at 85° C. The same portion of phosphorus oxychloride was added every hour at 85° C. for a total of 6 h. The crude mixture was poured into saturated aqueous sodium carbonate on ice, to reach pH 7-8. DCM was added. The mixture was filtered to remove inorganic salts and the organic layer was separated. The DCM layer was washed with brine and dried over anhydrous Na2SO4. Purification by ISCO chromatography (100% DCM) afforded 205 mg (29%) of the title compound as a white solid. 1H NMR (400 MHz, CD3OD): δ 9.31-9.36 (m, 1 H), 8.71 (d, J=5.8 Hz, 1 H), 7.93 (dd, J=5.6, 1.0 Hz, 1 H); MS (ESI): 239.42, 241.35 [M+H]+; HPLC tR=1.04 min (HPLC: Analytical—2 min).

Workup

  1. filtrationThe mixture was filtered
  2. customto remove inorganic salts
  3. customthe organic layer was separated
  4. washThe DCM layer was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customPurification by ISCO chromatography (100% DCM)

Sources & evidence

ORD record
ord-407068b3190b4cb5996bc98902894df4
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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