تفاعل #92792

ord-322ac2bbe2cc4c8b95d0a482635efc12

معادلة التفاعل

CC(C)(C)OC(=O)Nc1ccc2c(ccc3nc(C#N)sc32)c1
tert-butyl (2-cyanonaphtho[2,1-d]thiazol-7-yl)carbamate
CSc1ccccc1
thioanisole
O=C(O)C(F)(F)F
trifluoroacetic acid
N#Cc1nc2ccc3cc(N)ccc3c2s1
product
المردود 94.8%
N#Cc1nc2ccc3cc(N)ccc3c2s1
7-aminonaphtho[2,1-d]thiazole-2-carbonitrile
المردود 94.8%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    تركيزthe reaction was concentrated under reduced pressure

الإجراء التجريبي

To a stirred solution of tert-butyl (2-cyanonaphtho[2,1-d]thiazol-7-yl)carbamate (72 mg, 0.22 mmol) and thioanisole (0.5 mL) in 2 mL of DCM in an ice bath, 2 mL of trifluoroacetic acid was added. After 1 h, the reaction was concentrated under reduced pressure, and the product (47 mg, 94%) was isolated by silica gel chromatography eluting with 0→75% EtOAc in heptanes. 1H NMR (CD2Cl2) d 8.01 (d, 1H); 7.90 (dt, 1H); 7.76 (d, 1H); 7.09-7.16 (m, 2H).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09447450B2uspto-grants-2016_09