3,5-Dimethoxybenzaldehyde → HCID 16731290, compound

HRID 507341Notes

Reaction equation

HRID 507341 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[C:4]([O:14][CH2:15][CH:16]([OH:20])[CH2:17][NH:18][CH3:19])=[CH:3][CH:2]=1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([O:31][CH3:32])[CH:30]=1)[CH:26]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(O)(=O)C>[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[C:4]([O:14][CH2:15][CH:16]([OH:20])[CH2:17][N:18]([CH2:26][C:25]2[CH:28]=[C:29]([O:31][CH3:32])[CH:30]=[C:23]([O:22][CH3:21])[CH:24]=2)[CH3:19])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 817473,5-DimethoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58878128HCID 58878128, compound

Product 1

HCID 16731290HCID 16731290, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Procedure

The reaction of 1-(9H-carbazol-4-yloxy)-3-(methylamino)propan-2-ol (0.20 g, 0.74 mmol) with 3,5-dimethoxybenzaldehyde (0.185 g, 1.11 mmol) in the presence of 2-3 drops of glacial acetic acid and Na(OAc)3BH (0.157 g, 0.578 mmol) following the procedure similar to the one described in example 26, afforded the title compound as a brown colored paste (0.045 g, 13% yield) with 1H NMR (400 MHz, DMSO): δ 2.25(s, 3H), 3.40-3.60 (m, 2H), 3.51 (s, 2H), 3.65 (s, 6H), 4.10-4.13 (m, 1H), 4.15-4.25 (m, 2H), 5.00 (s, 1H), 6.31 (s, 1H), 6.49 (d, 2H, J=1.6 Hz), 6.67 (d, 1H, J=8.0 Hz), 7.05-7.12 (m, 2H), 7.25-7.35 (m, 2H), 7.43 (d, 1H, J=8 Hz), 8.17 (d, 1H, J=8.0 Hz), 11.23 (s, 1H). MS m/z: 421.0 (M+1).

Sources & evidence

ORD record
ord-397bd54d29194b7cb022bdc479372821
Source dataset
uspto-grants-2010_08
Patent number
US07786142B2

Reaction notes

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