1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 17952717, compound
Reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=O)=[C:2]1[CH:8]=O.COP([CH:16]([NH:20]C(=O)C)[C:17](=[O:19])[CH3:18])(=O)OC.N12CCCN=C1CCCCC2>>[S:1]1[C:2]2=[CH:8][N:20]=[C:16]([C:17](=[O:19])[CH3:18])[CH:6]=[C:3]2[CH:4]=[CH:5]1Participants
4
Procedure
Compounds of Formula I in which ring A is a thieno[2,3-c]pyridinyl can be prepared from a 2,3-thiophenedicarboxaldehyde (XLVI) (see Scheme X). The pyridinyl ring is formed by cooling a solution of the 2,3-thiophenedicarboxaldehyde (XLVI) in an organic solvent to about −10° C. to about 10° C., then adding about 1 eq. to about 1.5 eq. of (1-acetylamino-2-oxo-propyl)-phosphonic acid dimethyl ester (XLVII) and about 1 eq. to about 1.5 eq of a hindered aprotic base such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The solution is allowed to come to room temperature and is stirred for about 8 h to about 20 h to form 1-thieno[2,3-c]pyridin-5-yl-ethanone (XLVIII).
Workup
- customThe pyridinyl ring is formed
- customto come to room temperature
Sources & evidence
- ORD record
- ord-a43f854f2c7f42fa8912b080b0beca26
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07348359B2
Reaction notes
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