Morpholine → Methanol

HRID 1454007Notes

Reaction equation

HRID 1454007 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[Br:11][C:12]1[CH:13]=[C:14]([CH:22]=[CH:23][CH:24]=[O:25])[CH:15]=[C:16]([O:20][CH3:21])[C:17]=1[O:18][CH3:19].N1CC[O:29][CH2:28]C1>>[Br:11][C:12]1[CH:13]=[C:14]([CH:22]2[C:10]3[C:2](=[C:3]4[CH:4]=[CH:5][NH:6][C:7]4=[CH:8][CH:9]=3)[O:1][CH:24]([OH:25])[CH2:23]2)[CH:15]=[C:16]([O:20][CH3:21])[C:17]=1[O:18][CH3:19].[CH3:28][OH:29]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 754211H-indol-4-olHCID 858878623-(3-Bromo-4,5-dimethoxyphenyl)-propenal

Product 2

HCID 887MethanolYield 33%HCID 100926004-(3-Bromo-4,5-dimethoxyphenyl)-2-hydroxy-pyrrolo[2,3-h]chroman

Procedure

The title compound was prepared following the procedure described in Example 18 from 4-hydroxy indole (10 mg; 0.075 mmol) and 3-(3-bromo-4,5-dimethoxyphenyl)-propenal (20 mg; 0.074) using morpholine (7 μl) as a base in refluxing methanol (0.6 ml) (yield: 33% ). 1H NMR (acetone-d6): 10.16 (s, 1H), 7.20 (d, J=3.0 Hz) and 7.19 (d, J=2.5 Hz) (1H), 7.02 (broad d, J=2.0 Hz), 6.97 (broad signal) and 6.93 (d, J=1.8 Hz) (2H), 6.89 and 6.88 (d each, J =8.4 Hz; 1H), 6.49 (d, J=8.8 Hz), 6.47-6.48 (m) and 6.44 (d, J=8.4 Hz) (2H), 6.18 (d, J=6.8 Hz) and 6.10 (d, J=4.5 Hz) (1H), 5.68-5.71 and 5.56-5.62 (m each, 1H), 4.33-4.38 (broad dd, J=5.8, 9.9 Hz; 1H), 3.83, 3.81 and 3.79 (s each, 6H), 2.41 (ddd, J=2.0, 6.1, 12.9 Hz) and 2.08-2.26 (m) (2H).

Sources & evidence

ORD record
ord-95d6a86686314bb4aaba576cd5e9a2e7
Source dataset
uspto-grants-2009_01
Patent number
US07476741B2

Reaction notes

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