Tetramethyltin → HCID 10178849, compound

HRID 1269560Notes

Reaction equation

HRID 1269560 reaction equation
[C:1]([O:4]C1C=C(Cl)C(OC2C=CC(NC(=O)C(C)C)=C(Br)C=2)=C(Cl)C=1C)(=[O:3])[CH3:2].C[Sn](C)(C)C.C(O[C:37]1[CH:42]=[C:41]([Cl:43])[C:40]([O:44][C:45]2[CH:50]=[CH:49][C:48]([NH:51][C:52](=[O:56])[CH:53]([CH3:55])[CH3:54])=[C:47]([CH3:57])[CH:46]=2)=[C:39]([Cl:58])[C:38]=1C)(=O)C>[Cu]=O.CN(C)C=O>[Cl:43][C:41]1[CH:42]=[C:37]([CH2:2][C:1]([OH:4])=[O:3])[CH:38]=[C:39]([Cl:58])[C:40]=1[O:44][C:45]1[CH:50]=[CH:49][C:48]([NH:51][C:52](=[O:56])[CH:53]([CH3:55])[CH3:54])=[C:47]([CH3:57])[CH:46]=1

Participants

6

Reactant 3

HCID 11661TetramethyltinHCID 86592329HCID 86592329, compoundHCID 86592330HCID 86592330, compound

Product 1

HCID 10178849HCID 10178849, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalystHCID 6228DimethylformamideSolvent

Procedure

Methyl[3,5-dichloro-4-(3-bromo-4-isobutyramidophenoxy)phenyl] acetate (100 mg) was reacted with tetramethyltin (40 mg), dichloro(1,2-bis(diphenylphosphino)butane)palladium(II), copper(II) oxide (16 mg) and dimethylformamide (3 mL) using the method described in Example 3. This gave 20 mg (23%) of methyl(3,5-dichloro-4-[4-isobutyr-amido-3-methylphenoxy]phenyl) acetate, which was hydrolyzed using the method described in Example 1(i), to give 17 mg (88%) of 3,5-dichloro-4-(4-isobutyramido-3-methyl-phenoxy)phenylacetic acid, m/z 396.

Sources & evidence

ORD record
ord-9320e47ff90f4a66ab93875f28e7901e
Source dataset
uspto-grants-2007_04
Patent number
US07199265B2

Reaction notes

Loading…