3,5-Dimethoxybenzyl Bromide → 1-Butyl-5-chloro-3-(3,5-dimethoxybenzyl)-3-hydroxyindolin-2-one

HRID 1523085Notes

Reaction equation

HRID 1523085 reaction equation
C(N1C2C(=CC(C)=CC=2)C(O)([CH2:13][C:14]2[CH:19]=[C:18]([O:20][CH3:21])[C:17](OC)=[C:16]([O:24][CH3:25])[CH:15]=2)C1=O)C.C([O:36][CH:37]1[C:45]2[C:40](=[CH:41][CH:42]=[C:43]([Cl:46])[CH:44]=2)[N:39]([CH2:47][CH2:48][CH2:49][CH3:50])[C:38]1=[O:51])(=O)C1C=CC=CC=1.COC1C=C(C=C(OC)C=1)CBr>>[CH2:47]([N:39]1[C:40]2[C:45](=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=2)[C:37]([CH2:13][C:14]2[CH:15]=[C:16]([O:24][CH3:25])[CH:17]=[C:18]([O:20][CH3:21])[CH:19]=2)([OH:36])[C:38]1=[O:51])[CH2:48][CH2:49][CH3:50]

Participants

4

Reactant 3

HCID 12744903,5-Dimethoxybenzyl BromideHCID 863005421-Ethyl-3-hydroxy-5-methyl-3-(3,4,5-trimethoxybenzyl)indolin-2-oneHCID 904169811-Butyl-5-chloro-2-oxoindolin-3-yl benzoate

Product 1

HCID 863012751-Butyl-5-chloro-3-(3,5-dimethoxybenzyl)-3-hydroxyindolin-2-one

Procedure

This compound was made in an analogous fashion to 1-ethyl-3-hydroxy-5-methyl-3-(3,4,5-trimethoxybenzyl)indolin-2-one using 1-butyl-5-chloro-2-oxoindolin-3-yl benzoate and 3,5-dimethoxy benzyl bromide (purchased from Fisher Scientific). 1H NMR δ 7.25 (m, 2H) 6.61 (d, 1H), 6.24 (s, 1H), 6.06 (s, 2H), 3.66 (m, 7H), 3.23 (m, 2H), 3.16 (d, 1H), 1.63 (bs, OH), 1.35 (m, 2H), 1.17 (m, 2H), 0.96 (t, 3H). Calculated mass for C21H24ClNO4, 389.14. Observed 412.2 (M+Na).

Sources & evidence

ORD record
ord-a1bfd1c282f845928539b1c78083e370
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

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