Diethyl chlorophosphate → phosphoric acid diethyl ester 2-[4-(3-formyl-1-phenyl-1H-indol-2-yl)piperazin-1-yl]ethyl ester
Reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:12]3[C:17]([C:18]=2[CH:19]=[O:20])=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:6][CH2:5]1.[P:27](Cl)([O:32][CH2:33][CH3:34])([O:29][CH2:30][CH3:31])=[O:28]>>[CH:19]([C:18]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:10]=1[N:7]1[CH2:6][CH2:5][N:4]([CH2:3][CH2:2][O:1][P:27](=[O:28])([O:32][CH2:33][CH3:34])[O:29][CH2:30][CH3:31])[CH2:9][CH2:8]1)=[O:20]Participants
3
Procedure
2-[4-(2-Hydroxyethyl)piperazin-1-yl]-1-phenyl-1H-indole-3-carboxaldehyde is reacted with diethyl chlorophosphate as described in Step 1 of Example 31 to afford phosphoric acid diethyl ester 2-[4-(3-formyl-1-phenyl-1H-indol-2-yl)piperazin-1-yl]ethyl ester (71% yield) as a yellow solid. ESI/MS 486 (M+H); RT 2.94 min; NMR 10.15 (1H, s); 8.13 (1H, d, J=9 Hz); 7.68 (5H, m); 7.20 (2H, m); 6.91 (1H, d, J=6 Hz), 4.04 (6H, m); 3.28 (6H, m); 2.49 (4H, br s); 1.23 (6H, t).
Sources & evidence
- ORD record
- ord-d02069be19594bd9957b0df920ec0f6f
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07405300B2
Reaction notes
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