4-Bromo-2-iodoaniline → (R)-tert-butyl 2-((2-amino-5-bromophenyl)ethynyl)pyrrolidine-1-carboxylate

HRID 1481716Notes

Reaction equation

HRID 1481716 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4](I)[CH:3]=1.[C:10]([C@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])#[CH:11]>>[NH2:6][C:5]1[CH:7]=[CH:8][C:2]([Br:1])=[CH:3][C:4]=1[C:11]#[C:10][C@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]

Participants

3

Reactant 2

HCID 8239344-Bromo-2-iodoanilineHCID 10262067tert-butyl (2R)-2-ethynylpyrrolidine-1-carboxylate

Product 1

HCID 117844394(R)-tert-butyl 2-((2-amino-5-bromophenyl)ethynyl)pyrrolidine-1-carboxylateYield 89%

Procedure

(R)-tert-butyl 2-((2-amino-5-bromophenyl)ethynyl)pyrrolidine-1-carboxylate (4.32 g) was prepared via Sonogashira coupling according to the general procedure described in Example 156, Step 1, from 4-bromo-2-iodoaniline (3.96 g, 13.29 mmol) and (R)-tert-butyl 2-ethynylpyrrolidine-1-carboxylate (3.25 g, 16.64 mmol) in 89% yield.

Sources & evidence

ORD record
ord-9b531b4ab72449d4ba7b244d3ab0981a
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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