(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)boronic acid → 6-(5-Diethoxymethyl-furan-3-yl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

HRID 1635006Notes

Reaction equation

HRID 1635006 reaction equation
[CH3:1][C:2]1([CH3:16])[O:7][C:6](=[O:8])[NH:5][C:4]2[CH:9]=[CH:10][C:11](B(O)O)=[CH:12][C:3]1=2.Br[C:18]1[CH:22]=[C:21]([CH:23]([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])[O:20][CH:19]=1>>[CH2:28]([O:27][CH:23]([O:24][CH2:25][CH3:26])[C:21]1[O:20][CH:19]=[C:18]([C:11]2[CH:10]=[CH:9][C:4]3[NH:5][C:6](=[O:8])[O:7][C:2]([CH3:16])([CH3:1])[C:3]=3[CH:12]=2)[CH:22]=1)[CH3:29]

Participants

3

Reactant 2

HCID 10987806(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)boronic acidHCID 13995070HCID 13995070, compound

Product 1

HCID 235096166-(5-Diethoxymethyl-furan-3-yl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

Procedure

Prepared according to procedure B from 4,4-dimethyl 2 oxo -1,4-dihydro 2H-benzo[d][1,3]oxazine-6-boronic acid and 3-bromo-5-diethoxymehyl furan. A brown gum: 1H NMR (DMSO-d6) δ10.2 (s, 1H), 8.12(s, 1H), 7.54-7.49 (m, 2H), 6.93-6.88(m, 2H), 5.56(s, 1H), 3.60-3.38(m, 4H), 1.67(s ,6H), 1.2-1.14 (m, 6H). .MS (ESI) m/z 344 [M−H]−. Anal. Calcd. For C19H23NO51/2 H2O: C, 64.39; H, 6.77; N, 3.95. Found C, 64.90; H, 6.79; N, 3.78.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-4e258a52c8374abb99bcb4f082793adb
Source dataset
uspto-grants-2003_01
Patent number
US06509334B1

Reaction notes

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