Formaldehyde → 4-Bromo-3-(6-hydroxybenzo[d][1,3]dioxol-5-yl)-3-(hydroxymethyl)indolin-2-one

HRID 425532Notes

Reaction equation

HRID 425532 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:46]([OH:47])=[CH:45][C:41]3[O:42][CH2:43][O:44][C:40]=3[CH:39]=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:46]([OH:47])=[CH:45][C:41]3[O:42][CH2:43][O:44][C:40]=3[CH:39]=1)([CH2:19][OH:20])[C:31](=[O:37])[NH:32]2

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 7748Ethyl bromoacetateHCID 588725204-bromo-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-oneHCID 588725471-hexyl-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 588724444-Bromo-3-(6-hydroxybenzo[d][1,3]dioxol-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-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-one, and ethyl bromoacetate with para-formaldehyde, the title compound was obtained (70%) as a colorless solid: 1H NMR (300 MHz, DMSO-d6) δ 9.00 (br, 1H), 7.13-6.95 (m, 3H), 6.84 (d, 1H), 6.16 (d, 1H), 5.90-5.84 (m, 2H), 5.16-4.83 (m, 2H); 13C NMR (75 MHz, DMSO-d6) δ 177.8, 150.4, 147.1, 146.8, 139.8, 130.2, 129.3, 125.8, 117.7, 115.8, 109.3, 107.9, 101.2, 97.6, 63.5, 57.4.

Sources & evidence

ORD record
ord-9415752adb4341b381b34ba4cd2362e5
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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