Morpholine → 4-(3-Bromo-4,5-dimethoxyphenyl)-2-hydroxy-pyrido[3,4-h]chroman

HRID 1454009Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[Br:12][C:13]1[CH:14]=[C:15]([CH:23]=[CH:24][CH:25]=[O:26])[CH:16]=[C:17]([O:21][CH3:22])[C:18]=1[O:19][CH3:20].N1CCOCC1>>[Br:12][C:13]1[CH:14]=[C:15]([CH:23]2[C:11]3[C:2](=[C:3]4[CH:4]=[CH:5][N:6]=[CH:7][C:8]4=[CH:9][CH:10]=3)[O:1][CH:25]([OH:26])[CH2:24]2)[CH:16]=[C:17]([O:21][CH3:22])[C:18]=1[O:19][CH3:20]

Participants

Reactant 3

HCID 8083Morpholine

HCID 30386Isoquinolin-5-ol

HCID 858878623-(3-Bromo-4,5-dimethoxyphenyl)-propenal

Product 1

HCID 103871754-(3-Bromo-4,5-dimethoxyphenyl)-2-hydroxy-pyrido[3,4-h]chromanYield 29%

Procedure

The title compound was prepared following the procedure in Example 18 from 5-hydroxyisoquinoline (9 mg; 0.062 mmol) and 3-(3-bromo-4,5-dimethoxyphenyl)-propenal (30 mg; 0.11 mmol) using morpholine as a base (10 μl; 0.11 mmol) (yield: 29%). 1H NMR (acetone-d6): 9.16 (s, 1H), 8.50 and 8.49 (d each, J=5.7 Hz; 1H), 7.95 (d, J=6.4 Hz) and 7.94 (d, J=5.9 Hz) (1H), 7.51 (d, J=8.4 Hz) and 7.49 (d, J=7.0 Hz) (1H), 6.98-7.07 (m, 3H), 6.65 (d, J=6.6 Hz) and 6.59 (d, J=3.9 Hz) (1H), 5.91-5.93 (m) and 5.74-5.77 (m) (1H), 4.46-4.54 (overlapping dd, J=6.2, 10.5 Hz; 1H), 3.84, 3.81 and 3.80 (s each, 6H), 2.54 (ddd, J=2.1, 6.4, 13.3 Hz) and 2.19-2.38 (m) (2H).

Sources & evidence

ORD record: ord-5c6521a9cb5442f581fcbd96148ca30b
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07476741B2

Reaction notes

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