tert-Butyl bromoacetate → tert-Butyl 3-amino-1H-indole-2-carboxylate

HRID 1376105Notes

Reaction equation

HRID 1376105 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9]C(=O)C(F)(F)F)#[N:2].Br[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>>[NH2:2][C:1]1[C:3]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:9][C:17]=1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]

Participants

3

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 9203669HCID 9203669, compound

Product 1

HCID 19360138tert-Butyl 3-amino-1H-indole-2-carboxylate

Procedure

Follow the procedure of Example 3 (Steps B3–B5) but start with N-(2-cyano-phenyl)-2,2,2-trifluoroacetamide (synthesis described in J. Fluorine Chem. 1981, 18, (2), 185–95) and tert-butyl bromoacetate to obtain the title compound: MS 310(M+H), TLC (silica gel, dichloromethane/methanol, 7:1) Rf=0.38.

Sources & evidence

ORD record
ord-fca8227adf7b42cdaf49f66008a2082d
Source dataset
uspto-grants-2007_01
Patent number
US07169925B2

Reaction notes

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