Diethyl Ether → 2-Cyclopropyl-4-methoxybenzothiazole-7-carboxylic acid

HRID 427290Notes

Reaction equation

HRID 427290 reaction equation
Br[C:2]1[C:10]2[S:9][C:8]([CH:11]3[CH2:13][CH2:12]3)=[N:7][C:6]=2[C:5]([O:14][CH3:15])=[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:54][CH2:55]C)C.[O:57]1CCCC1>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:11]1([C:8]2[S:9][C:10]3[C:2]([C:55]([OH:54])=[O:57])=[CH:3][CH:4]=[C:5]([O:14][CH3:15])[C:6]=3[N:7]=2)[CH2:13][CH2:12]1

Participants

8

Reactant 5

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 12091099Phosphine, (1-methylethylidene)bis[diphenyl-HCID 183570107-Bromo-2-cyclopropyl-4-methoxybenzothiazole

Product 1

HCID 183570082-Cyclopropyl-4-methoxybenzothiazole-7-carboxylic acid

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

Starting from 7-bromo-2-cyclopropyl-4-methoxybenzothiazole (515 mg), palladium (II) acetate (40 mg), bis-diphenylphosphinopropane (149 mg), and triethylamine (2.5 ml) in tetrahydrofuran (15 ml) and water (7 ml). Trituration of the residue with diethyl ether yielded the title compound as an off-white solid (360 mg). TLC Rf 0.49 (ethyl acetate).

Sources & evidence

ORD record
ord-d00d9a31b52c484f805a0686f04fa8f5
Source dataset
uspto-grants-2001_11
Patent number
US06313116B1

Reaction notes

Loading…