Isatin → HCID 58914706, compound

HRID 1297766Notes

Reaction equation

[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].[CH3:12][C:13]1[CH:14]=[C:15]([Mg]Br)[CH:16]=[C:17]([CH3:21])[C:18]=1[O:19][CH3:20].C1COCC1>>[OH:5][C:4]1([C:15]2[CH:16]=[C:17]([CH3:21])[C:18]([O:19][CH3:20])=[C:13]([CH3:12])[CH:14]=2)[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[NH:1][C:2]1=[O:3]

Participants

Reactant 3

HCID 7054Isatin

HCID 8028Tetrahydrofuran

HCID 178490746HCID 178490746, compound

Product 1

HCID 58914706HCID 58914706, compoundYield 84%

Procedure

Using a method similar to Preparation 18 with isatin (1.77 g, 12 mmol) a 0.5M solution of 3,5-dimethyl-4-methoxyphenylmagnesium bromide in THF (50 mL, 25 mmol) gives 2.70 g (84%) of a yellow solid. MS (ES): m/z=266 (M+1−H2O), 282 (M−1); 1H NMR(DMSO-d6): δ10.35 (s, 1H), 7.24 (dt, J=1.3 Hz, J=7.6 Hz, 1H), 7.10 (d, J=6.4 Hz, 1H), 6.98 (dd, J=0.9 Hz, J=7.5 Hz, 1H), 6.90 (m, 3H), 6.50 (s, 1H), 3.62 (s, 3H), 2.17 (s, 6H).

Sources & evidence

ORD record: ord-bae14fb10d5e403c979951e250915aef
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250442B2

Reaction notes

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