Butanal → HCID 4254842, compound

HRID 528898Notes

Reaction equation

HRID 528898 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH2:11][NH2:12].[CH:13](=O)[CH2:14][CH2:15][CH3:16]>>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH2:11][NH:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

3

Reactant 2

HCID 261ButanalHCID 141969461-(1-Methyl-1H-indol-2-yl)methanamine

Product 1

HCID 4254842HCID 4254842, compoundYield 10.4%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 137, (1-methyl-1H-indol-2-yl)methanamine (500 mg, 3.12 mmol) and butyraldehyde (310 μL, 3.43 mmol) were converted to the title compound (70 mg, 6%). 1H NMR (CDCl3) δ 7.62-7.54 (m, 1H), 7.36-7.27 (m, 1H), 7.27-7.16 (m, 1H), 7.17-7.03 (m, 1H), 6.50 (s, 1H), 4.05 (s, 2H), 3.77 (s, 3H), 2.82-2.70 (m, 2H), 1.60 (ddd, J=15.1, 7.5, 7.4 Hz, 2H), 1.45-1.16 (m, 2H), 0.96-0.87 (m, 3H).

Sources & evidence

ORD record
ord-e6a6ce7b62fe483987c368a85c6e6665
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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