7-chloro-2-[(S)-2-(methoxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridine → Methyl 6-[(2-{[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]carbonyl}thieno[3,2-b]pyridin-7-yl)oxy]-2-methylbenzo[b]thiophene-3-carboxylate
Reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([CH3:14])[S:7][C:6]=2[CH:15]=1.Cl[C:17]1[CH:22]=[CH:21][N:20]=[C:19]2[CH:23]=[C:24]([C:26]([N:28]3[CH2:32][CH2:31][CH2:30][C@H:29]3[CH2:33][O:34][CH3:35])=[O:27])[S:25][C:18]=12>>[CH3:35][O:34][CH2:33][C@@H:29]1[CH2:30][CH2:31][CH2:32][N:28]1[C:26]([C:24]1[S:25][C:18]2[C:19](=[N:20][CH:21]=[CH:22][C:17]=2[O:1][C:2]2[CH:3]=[CH:4][C:5]3[C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([CH3:14])[S:7][C:6]=3[CH:15]=2)[CH:23]=1)=[O:27]Participants
3
Procedure
This material was prepared from the reaction of methyl 6-hydroxy-2-methylbenzo[b]thiophene-3-carboxylate 11a (85.8 mg, 0.386 mmole) with 7-chloro-2-{[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]carbonyl}thieno[3,2-b]pyridine 2a (100 mg, 0.322 mmole) and CS2CO3 (524 mg, 1.61 mmole) in a manner similar to that previously described for example 1 to give a brown solid (64 mg,40%). 1H NMR (DMSO-d6, 300 MHz) δ8.70 (1H, d, J=4.90 Hz), 8.51 (1H, d, J=9.04 Hz), 8.15 (1H, s), 8.14 (1H, s), 7.54 (1H, dd, J=2.17, 8.95 Hz), 6.91 (1H, d, J=5.46 Hz), 4.47-4.38 (1H, m), 4.07-3.90 (2H, m), 4.03 (3H, s), 3.72-3.50 (2H, m), 3.42, 3.39 (3H, s), 2.94 (3H, s), 2.21-1.93 (4H, m).
Sources & evidence
- ORD record
- ord-1fb33ddca63144389e32a10e4f9f588f
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06869962B2
Reaction notes
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