Morpholine → 2-Hydroxy-7-methyl-4-(3,4,5-trimethoxyphenyl)-pyrrolo[2,3-h]chroman

HRID 1454008Notes

Reaction equation

HRID 1454008 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[CH3:11].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:24]=[CH:25][CH:26]=[O:27])[CH:17]=[C:18]([O:22][CH3:23])[C:19]=1[O:20][CH3:21].N1CCOCC1>>[OH:27][CH:26]1[CH2:25][CH:24]([C:16]2[CH:17]=[C:18]([O:22][CH3:23])[C:19]([O:20][CH3:21])=[C:14]([O:13][CH3:12])[CH:15]=2)[C:10]2[C:2](=[C:3]3[CH:4]=[CH:5][N:6]([CH3:11])[C:7]3=[CH:8][CH:9]=2)[O:1]1

Participants

4

Reactant 3

HCID 8083MorpholineHCID 367983-(3,4,5-Trimethoxyphenyl)-2-propenalHCID 158257394-Hydroxy-1-methylindole

Product 1

HCID 100904802-Hydroxy-7-methyl-4-(3,4,5-trimethoxyphenyl)-pyrrolo[2,3-h]chromanYield 48%

Procedure

The title compound was prepared following the procedure described in Example 18 using 4-hydroxy-N-methyl indole (15 mg; 0.1 mmol) and 3-(3,4,5-trimethoxy-phenyl)-propenal (25 mg; 0.11 mmol) with morpholine (10 μl; 0.11 mmol) as a base (yield: 48%). 1H NMR (acetone-d6) 6.96 (d, J=2.7 Hz) and 6.94 (d, J=3.1 Hz) (1H), 6.70 (d, J=8.2 Hz) and 6.68 (d, J=7.2 Hz) (1H), 6.45 (d, J=8.6 Hz), 6.43 (s) and 6.40 (d, J=9.0 Hz) (3H), 6.29 and 6.28 (d each, J=3.3 Hz, 1H), 6.01 (d, J=6.8 Hz) and 5.91 (d, J=4.3 Hz) (1H), 5.57-5.60 (m) and 5.42-5.44 (m) (1H), 4.19 (dd, J=6.2, 10.0 Hz; 1H), 3.63, 3.62 and 3.59 (s each, 12 H), 2.23-2.28 (m) and 2.00-2.11 (m) (2H).

Sources & evidence

ORD record
ord-21b2841b7bb34be09b6f776261371170
Source dataset
uspto-grants-2009_01
Patent number
US07476741B2

Reaction notes

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