4,7-dichloro-3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-indol-2-one → HCID 59263423, compound

HRID 425626Notes

Reaction equation

HRID 425626 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2([CH2:25]O)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:10]2=[O:24])=[C:4]([OH:27])[CH:3]=1.ClC1C=CC(Cl)=C2C=1C(C1C(O)=CC3OCOC=3C=1)(CO)C(=O)N2CCCCC>>[F:8][C:7]1[C:2]([F:1])=[CH:3][C:4]2[O:27][CH2:25][C:9]3([C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[N:11]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:10]3=[O:24])[C:5]=2[CH:6]=1

Participants

3

Reactant 2

HCID 588724744,7-dichloro-3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-indol-2-oneHCID 58872499HCID 58872499, compound

Product 1

HCID 59263423HCID 59263423, compoundYield 46%

Procedure

Following the procedure as described in EXAMPLE 1.22, and making non-critical variations using ethyl [3-(4,5-difluoro-2-hydroxyphenyl)-3-(hydroxymethyl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate to replace 4,7-dichloro-3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-indol-2-one, the title compound was obtained in 46% yield as a light yellow oil: 1H NMR (300 MHz, CDCl3) δ 7.31 (dt, 1H), 7.16 (dd, 1H), 7.08 (dt, 1H), 6.81-6.71 (m, 2H), 6.67 (dd, 1H), 4.98 (d, 1H), 4.74 (d, 1H), 4.64 (d, 1H), 4.37 (d, 4.24 (q, 7.1 Hz), 1.28 (t, 3H); MS (ES+) m/z 360.5 (M+1).

Sources & evidence

ORD record
ord-db8e85c3e21842628758ea9343d6ee38
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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