2-Bromoethanol → 7-(2-Hydroxy-ethyl)-3-iodo-2-phenyl-7H-pyrano[2,3-c]pyridine-4,8-dione
Reaction equation
[I:1][C:2]1[C:3](=[O:20])[C:4]2[CH:9]=[CH:8][N:7]([CH3:10])[C:6](=[O:11])[C:5]=2[O:12][C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.IC1C(=O)C2C=CN[C:26](=[O:30])C=2OC=1C1C=CC=CC=1.BrCCO>>[OH:30][CH2:26][CH2:10][N:7]1[CH:8]=[CH:9][C:4]2[C:3](=[O:20])[C:2]([I:1])=[C:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[O:12][C:5]=2[C:6]1=[O:11]Participants
4
Procedure
Following the procedure used to prepare 3-iodo-7-methyl-2-phenyl-7H-pyrano[2,3-c]pyridine-4,8-dione, 3-iodo-2-phenyl-7H-pyrano[2,3-c]pyridine-4,8-dione was reacted with 2-bromoethanol to give the title compound (45.2 mg, 81%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.76-7.73 (m, 2H), 7.65 (d, J=7.3 Hz, 1H), 7.62-7.58 (m, 3H), 6.64 (d, J=7.3 Hz, 1H), 4.93 (t, J=5.5 Hz, 1H), 4.06 (t, J=5.4 Hz, 2H), 3.67 (q, J=5.4 Hz, 211).
Sources & evidence
- ORD record
- ord-d66f6ada7ea7499dad50461363ec46fc
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546376B2
Reaction notes
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