Phosphorus oxide (P4O10) → 2-Bromo-6,7-dihydrothieno[3,2-c]pyridin-4(5H)-one

HRID 1843856Notes

Reaction equation

HRID 1843856 reaction equation
C([O:3][C:4](=O)[NH:5][CH2:6][CH2:7][C:8]1[S:9][C:10]([Br:13])=[CH:11][CH:12]=1)C.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O=P(Cl)(Cl)Cl>[Br:13][C:10]1[S:9][C:8]2[CH2:7][CH2:6][NH:5][C:4](=[O:3])[C:12]=2[CH:11]=1

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 66803815HCID 66803815, compound

Product 1

HCID 569722892-Bromo-6,7-dihydrothieno[3,2-c]pyridin-4(5H)-oneYield 37.56%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

Using analogous reaction conditions and workup as described in example 1, step 4, [2-(5-bromo-thiophen-2-yl)-ethyl]-carbamic acid ethyl ester (I-14c: 2.7 g, 9.8 mmol) in POCl3 (20 mL) was reacted with P2O5 (2.7 g, 19.64 mmol) to afford the crude product. Purification by column chromatography on silica gel (0.5% methanol in DCM) afforded 850 mg of the product (37.56% yield).

Workup

  1. customreaction conditions and workup
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (0.5% methanol in DCM)

Sources & evidence

ORD record
ord-311408b0712a454ca902c20ece4679e5
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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