Phosphorus oxide (P4O10) → 6.7-dihydrothieno[3.2.c]pyridin-4(5H)-one

HRID 1843833Notes

Reaction equation

HRID 1843833 reaction equation
C([O:3][C:4](=O)[NH:5][CH2:6][CH2:7][C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)C.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O=P(Cl)(Cl)Cl>[S:9]1[C:8]2[CH2:7][CH2:6][NH:5][C:4](=[O:3])[C:12]=2[CH:11]=[CH:10]1

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 10867324HCID 10867324, compound

Product 1

HCID 203468586.7-dihydrothieno[3.2.c]pyridin-4(5H)-oneYield 33.5%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
110 °C

Procedure

Using an analogous procedure and workup as described in Example 1, step 4, (2-thiophen-2-yl-ethyl)-carbamic acid ethyl ester (I-7c: 800 mg, 3.50887 mmol) in POCl3 (10 mL) was reacted with P2O5 (996 mg, 7.0175 mmol). The resulting mixture was stirred at 110° C. for 4 hours to afford the crude product. Purification by column chromatography on silica gel (2% methanol in CHCl3) afforded 180 mg of the product (33.5% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (2% methanol in CHCl3)

Sources & evidence

ORD record
ord-375c703fe5ff4d3ca211665eb22edbee
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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