3,4-Dimethoxyphenylboronic acid → 2-(3,4-Dimethoxyphenyl)-2-(1,3-dioxoisoindolin-5-ylamino)acetic acid

HRID 1515512Notes

Reaction equation

HRID 1515512 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:11][CH:12]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=2)[C:13]([OH:15])=[O:14])[CH:7]=[CH:8][C:9]=1F)(=[O:3])[NH2:2].N=C1C=CC2[C:32](=[O:36])NC(=O)C=2C1.COC1C=C(B(O)O)C=CC=1OC.O.C(O)(=O)C=O>>[CH3:25][O:24][C:18]1[CH:17]=[C:16]([CH:12]([NH:11][C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[C:32](=[O:36])[NH:2][C:1]3=[O:3])[C:13]([OH:15])=[O:14])[CH:21]=[CH:20][C:19]=1[O:22][CH3:23]

Participants

5

Reactant 4

HCID 27347023,4-Dimethoxyphenylboronic acidHCID 15620607Glyoxylic acid, monohydrateHCID 594793922-(3-Carbamoyl-4-fluorophenylamino)-2-(3,4-dimethoxyphenyl)acetic acidHCID 68106733HCID 68106733, compound

Product 1

HCID 594794702-(3,4-Dimethoxyphenyl)-2-(1,3-dioxoisoindolin-5-ylamino)acetic acidYield 88%

Procedure

17A was prepared in a procedure similar to that of 13A using 5-iminoisoindoline-1,3-dione, 3,4-dimethoxyphenylboronic acid and glyoxylic acid monohydrate. Yield: 88%. 1H NMR (400 MHz, Methanol-d4) δ ppm 3.82 (s, 3H) 3.83 (s, 3H) 5.17 (s, 1H) 6.90 (dd, J=8.35, 2.20 Hz, 1H) 6.95 (d, J=7.91 Hz, 1H) 6.99 (d, J=2.20 Hz, 1H) 7.07-7.10 (m, 1H) 7.13 (d, J=2.20 Hz, 1H) 7.50 (d, J=8.35 Hz, 1H), LCMS: 366 (M+1).

Sources & evidence

ORD record
ord-881bd93e3a2f4ff7809bc5c5a5667866
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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