Diethyl Ether → 2-(Piperidin-1-yl)-4-methoxybenzothiazole-7-carboxylic acid

HRID 427291Notes

Reaction equation

HRID 427291 reaction equation
Br[C:2]1[C:10]2[S:9][C:8]([N:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)=[N:7][C:6]=2[C:5]([O:17][CH3:18])=[CH:4][CH:3]=1.C1(P(C(P(C2C=CC=CC=2)C2C=CC=CC=2)(C)C)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.C([O:57][CH2:58]C)C.[O:60]1CCCC1>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:11]1([C:8]2[S:9][C:10]3[C:2]([C:58]([OH:57])=[O:60])=[CH:3][CH:4]=[C:5]([O:17][CH3:18])[C:6]=3[N:7]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

8

Reactant 5

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 12091099Phosphine, (1-methylethylidene)bis[diphenyl-HCID 183570097-Bromo-2-(piperidin-1-yl)-4-methoxybenzothiazole

Product 1

HCID 183569982-(Piperidin-1-yl)-4-methoxybenzothiazole-7-carboxylic acid

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

Starting from 7-bromo-2-(piperidin-1-yl)-4-methoxybenzothiazole (1.4 g), palladium (II) acetate (100 mg), bis-diphenylphosphinopropane (350 mg), and triethylamine (6 ml) in tetrahydrofuran (200 ml) and water (20 ml). Trituration ofthe residue with diethyl ether yielded the title compound as a yellow solid (700 mg). TLC Rf 0.66 (ethyl acetate).

Sources & evidence

ORD record
ord-673132dfd144492887af786fe497a62c
Source dataset
uspto-grants-2001_11
Patent number
US06313116B1

Reaction notes

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