Piperonal → 6-Benzyloxy-4-methyl-1H-indole-2-carboxylic acid

HRID 62654Notes

Reaction equation

HRID 62654 reaction equation
O1C2=CC3C=[C:9]([C:13]([OH:15])=[O:14])[NH:10]C=3C=C2OC1.[CH2:16]([O:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[C:26]([CH3:32])[CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O1C2C=CC(C=O)=CC=2OC1>>[CH2:16]([O:23][C:24]1[CH:31]=[C:30]2[C:27]([CH:28]=[C:9]([C:13]([OH:15])=[O:14])[NH:10]2)=[C:26]([CH3:32])[CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 8438PiperonalHCID 9073915H-[1,3]dioxolo[4,5-f]indole-6-carboxylic acidHCID 27598062-Methyl 4-benzyloxybenzaldehyde

Product 1

HCID 692802316-Benzyloxy-4-methyl-1H-indole-2-carboxylic acid

Procedure

Intermediate I-5a was prepared using procedures analogous to those described above for the synthesis of 5H-[1,3]dioxolo[4,5-f]indole-6-carboxylic acid (I-4c) using 4-(benzyloxy)-2-methylbenzaldehyde (I-4c) as the starting material instead of benzo[d][1,3]dioxole-5-carbaldehyde. ESI MS: m/z 282.24 (M+H).

Workup

  1. customIntermediate I-5a was prepared

Sources & evidence

ORD record
ord-1afba8ef7f84416c8027ab29ea0dea06
Source dataset
uspto-grants-2016_09
Patent number
US09447039B2

Reaction notes

Loading…