Cesium carbonate → HCID 69007075, compound

HRID 2102511Notes

Reaction equation

HRID 2102511 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3](=[O:11])[CH2:2]1.Br[CH2:13][C@H:14]([CH3:24])[CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Si:17]([O:16][CH2:15][CH:14]([CH3:24])[CH2:13][C@H:2]1[C:3](=[O:11])[NH:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[O:1]1)([C:20]([CH3:21])([CH3:22])[CH3:23])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 727572H-1,4-benzoxazin-3(4H)-oneHCID 14608666HCID 14608666, compound

Product 1

HCID 69007075HCID 69007075, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4H-Benzo[1,4]oxazin-3-one (2.47 g, 16.5 mmol), (R)-(3-bromo-2-methylpropoxy)-tert-butyldimethylsilane (95MF94) (4.01 g, 15.0 mmol) and Cs2CO3 (12.2 g, 37.6 mmol) in DMF (20 mL) were reacted according to GP2 to give the title compound (108LM24-21) (3.92 g, 78%). 1H NMR (CDCl3) δ 7.15-7.11 (m, 1H), 6.99-6.91 (m, 3H), 4.60-4.50 (m, 2H), 3.98 (dd, J=8.3 Hz, J=12.4 Hz, 1H), 3.81 (dd, J=5.5 Hz, J=12.4 Hz, 1H), 3.51 (dd, J=4.1 Hz, J=9.7 Hz, 1H), 3.40 (dd, J=6.9 Hz, J=9.7 Hz, 1H), 2.12-2.02 (m, 1H), 0.90-0.82 (m, 12H), 0.02 (s, 6H).

Sources & evidence

ORD record
ord-215e92e6a7ef4c7ea3b847ad6ee3f701
Source dataset
uspto-grants-2009_08
Patent number
US07576078B2

Reaction notes

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