Bromomethylcyclopropane → Indole

HRID 1685588Notes

Reaction equation

HRID 1685588 reaction equation
FC(F)(F)[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1.C1(CBr)CC1.C(OC(=O)C(SC1SC(N)=NC=1)C)C.C(OC(=O)CSC1SC(N)=NC=1)C.C1(CN2C3C(=CC=C(F)C=3)C(C(NC3SC=C(SCC(O)=O)N=3)=O)=C2)CC1>>[NH:9]1[C:10]2[C:6](=[CH:5][CH:4]=[CH:3][CH:11]=2)[CH:7]=[CH:8]1

Participants

6

Reactant 5

HCID 81503BromomethylcyclopropaneHCID 27775236-(Trifluoromethyl)indoleHCID 21455623Ethyl 2-(2-aminothiazol-5-ylthio)acetateHCID 86610210{2-[(1-Cyclopropylmethyl-6-fluoro-1H-indole-3-carbonyl)-amino]-thiazol-4-ylsulfanyl}-acetic acidHCID 86610213(2-Aminothiazole-5-ylsulfanyl)-propionic acid ethyl ester

Product 1

HCID 798Indole

Procedure

6-trifluoromethylindole, R5X=cyclopropyl-methylbromide; NH2A=(2-amino-thiazole-5-ylsulfanyl)-propionic acid ethyl ester (prepared according to the procedure for the synthesis of (2-amino-thiazole-5-ylsulfanyl)-acetic acid ethyl ester described under the procedure for the synthesis of {2-[(1-Cyclopropylmethyl-6-fluoro-1H-indole-3-carbonyl)-amino]-thiazol-4-ylsulfanyl}-acetic acid.

Sources & evidence

ORD record
ord-769917b19b8443268b1c41989eb04abc
Source dataset
uspto-grants-2012_04
Patent number
US08148413B2

Reaction notes

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