1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 17952717, compound

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Reaction Steps

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).

Provenance & Evidence