3-(Bromomethyl)furan → 4-(1-furan-3-ylmethyl-1H-pyrrolo[2,3-b]pyridin-3-yl) piperidine-1-carboxylic acid ethyl ester

HRID 1437159Notes

Reaction equation

HRID 1437159 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].Br[CH2:22][C:23]1[CH:27]=[CH:26][O:25][CH:24]=1>C(OCC)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:22][C:23]3[CH:27]=[CH:26][O:25][CH:24]=3)[CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 110949343-(Bromomethyl)furanHCID 49759051Ethyl 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylate

Product 1

HCID 688947724-(1-furan-3-ylmethyl-1H-pyrrolo[2,3-b]pyridin-3-yl) piperidine-1-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

This compound was prepared following the procedure described in example 1, part F, starting with 1.22 g (4.46 mmol) of 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylic acid ethyl ester and 6.3 ml (6.24 mmol) of a freshly prepared 1 M solution of 3-bromomethylfuran in ethyl ether. The crude mixture was stirred at 60° C. for 3 hours. After standard work-up, 1 g (63% of yield) of the expected product was isolated.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-182967d8802343159e974e8bfff427f1
Source dataset
uspto-grants-2009_11
Patent number
US07622480B2

Reaction notes

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