Formaldehyde → 4-Bromo-3-(6-hydroxy-2,3-dihydrobenzofuran-5-yl)-3-(hydroxymethyl)indolin-2-one

HRID 1259629Notes

Reaction equation

C(N1C2C(=CC=CC=2)C(C2C(O)=C[C:19]3[O:20]COC=3C=2)C1=O)CCCCC.[Br:27][C:28]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:29]=1[CH:30]([C:38]1[C:39]([OH:47])=[CH:40][C:41]3[O:45][CH2:44][CH2:43][C:42]=3[CH:46]=1)[C:31](=[O:37])[NH:32]2.BrCC(OCC)=O.C=O>>[Br:27][C:28]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:29]=1[C:30]([C:38]1[C:39]([OH:47])=[CH:40][C:41]3[O:45][CH2:44][CH2:43][C:42]=3[CH:46]=1)([CH2:19][OH:20])[C:31](=[O:37])[NH:32]2

Participants

Reactant 4

HCID 712Formaldehyde

HCID 7748Ethyl bromoacetate

HCID 120044054-bromo-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-1,3-dihydro-2H-indol-2-one

HCID 588725471-hexyl-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 588724384-Bromo-3-(6-hydroxy-2,3-dihydrobenzofuran-5-yl)-3-(hydroxymethyl)indolin-2-one

Procedure

Following the procedure as described in PREPARATION 31D, and making non-critical variations to replace 1-hexyl-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-one with 4-bromo-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-1,3-dihydro-2H-indol-2-one, and ethyl bromoacetate with para-formaldehyde, the title compound was obtained that was used directly for further reaction.

Sources & evidence

ORD record: ord-7d681d3e45564536b306c36e333a0a23
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466188B2

Reaction notes

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