Dibutyltin dichloride → 2-(4-Trifluoromethoxy-phenyl)-benzothiazole-6-carboxylic acid (2-aminophenyl)-amide

HRID 416241Notes

Reaction equation

HRID 416241 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[CH:26]=[CH:25][C:20]2[N:21]=[C:22](N)[S:23][C:19]=2[CH:18]=1)=[O:16])(C)(C)C.[F:28][C:29]([F:40])([F:39])[O:30][C:31]1[CH:38]=[CH:37][C:34](C=O)=[CH:33][CH:32]=1.C([Sn](Cl)(Cl)CCCC)CCC.C1([SiH3])C=CC=CC=1>C1COCC1>[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[CH:26]=[CH:25][C:20]2[N:21]=[C:22]([C:34]3[CH:33]=[CH:32][C:31]([O:30][C:29]([F:28])([F:39])[F:40])=[CH:38][CH:37]=3)[S:23][C:19]=2[CH:18]=1)=[O:16]

Participants

6

Reactant 4

HCID 12688Dibutyltin dichlorideHCID 12752Phenylsilane2×HCID 69573p-(Trifluoromethoxy)benzaldehydeHCID 58930649{2-[(2-Amino-benzothiazole-6-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester

Product 1

HCID 666221852-(4-Trifluoromethoxy-phenyl)-benzothiazole-6-carboxylic acid (2-aminophenyl)-amideYield 93.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 115 (300 mg, 0.78 mmol), 4-(trifluoromethoxy)benzaldehyde (123 μl, 0.86 mmol), and dibutyltin dichloride (24 mg, 0.08 mmol) in THF was added phenylsilane (106 μl, 0.86 mmol). The mixture was stirred overnight at room temperature under nitrogen, additional aldehyde and phenylsilane were added and the stirring continued until no more starting material was present. The THF was evaporated off the mixture and the residue was purified by flash column chromatography (EtOAc/hexane 30/70, then 50/50), to give the title compound 116 (314 mg, 72%). 1H-NMR (DMSO) δ: 9.77 (s, 1H), 8.89 (t, J=5.7 Hz, 1H); 8.69 (s, 1H); 8.29 (d, J=1.8 Hz, 1H); 7.84 (dd, J=8.4, 1.8 Hz, 1H); 7.50 (m, 5H); 7.37 (d, J=7.8 Hz, 2H); 7.17 (m, 2H); 4.69 (d, J=5.7 Hz, 2H); 1.47 (s, 9H).

Workup

  1. customThe THF was evaporated off the mixture
  2. customthe residue was purified by flash column chromatography (EtOAc/hexane 30/70

Sources & evidence

ORD record
ord-59ca4d0e133e41ba887e1831d0fefbac
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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