Sodium hydride → 3-Bromo-5-[(S)-2-(2,2,2-trifluoro-ethoxymethyl)-pyrrolidin-1-ylmethyl]-pyridine

HRID 1774749Notes

Reaction equation

HRID 1774749 reaction equation
[F:1][C:2]([F:12])([F:11])[CH2:3][O:4][CH2:5][C@@H:6]1[CH2:10][CH2:9][CH2:8][NH:7]1.[Br:13][C:14]1[CH:15]=[N:16][CH:17]=[C:18]([CH2:20]Cl)[CH:19]=1.[H-].[Na+]>>[Br:13][C:14]1[CH:15]=[N:16][CH:17]=[C:18]([CH2:20][N:7]2[CH2:8][CH2:9][CH2:10][C@H:6]2[CH2:5][O:4][CH2:3][C:2]([F:1])([F:11])[F:12])[CH:19]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 117012593-Bromo-5-(chloromethyl)pyridineHCID 86679128(S)-2-(2,2,2-Trifluoro-ethoxymethyl)-pyrrolidine

Product 1

HCID 866791293-Bromo-5-[(S)-2-(2,2,2-trifluoro-ethoxymethyl)-pyrrolidin-1-ylmethyl]-pyridine

Procedure

In analogy to the procedure described for the preparation of intermediates A-12 [B], (S)-2-(2,2,2-trifluoro-ethoxymethyl)-pyrrolidine was reacted with 3-bromo-5-chloromethyl-pyridine (intermediate A-12 [A]) in presence of NaH to give the title compound as a yellow oil. MS: 353.1, 355.1 (M+H+).

Sources & evidence

ORD record
ord-feec67488d17445cb0ef7366d4c3e273
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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