Tert-butyl 4-[2-(4-cyano-3-fluorophenoxymethyl)pyridin-5-yl]piperidine-1-carboxylate → 2-[4-[2-(4-Cyano-3-fluorophenoxymethyl)pyridin-5-yl]piperidin-1-yl]-5-ethylpyrimidine
Reaction equation
[C:1]([C:3]1[CH:29]=[CH:28][C:6]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[CH2:20][CH2:19][N:18]([C:21](OC(C)(C)C)=O)[CH2:17][CH2:16]3)=[CH:11][N:10]=2)=[CH:5][C:4]=1[F:30])#[N:2].[CH2:31]([C:33]1[CH:34]=[N:35]C(Br)=[N:37][CH:38]=1)[CH3:32]>>[C:1]([C:3]1[CH:29]=[CH:28][C:6]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[CH2:16][CH2:17][N:18]([C:21]4[N:37]=[CH:38][C:33]([CH2:31][CH3:32])=[CH:34][N:35]=4)[CH2:19][CH2:20]3)=[CH:11][N:10]=2)=[CH:5][C:4]=1[F:30])#[N:2]Participants
3
Procedure
The title compound was prepared from tert-butyl 4-[2-(4-cyano-3-fluorophenoxymethyl)pyridin-5-yl]piperidine-1-carboxylate (Example 13) (50 mg, 0.12 mmol) and 5-ethyl-2-bromopyrimidine (29 μL, 0.24 mmol) following a procedure analogous to that in Example 48 as a white crystal (37 mg, yield 73%).
Sources & evidence
- ORD record
- ord-bd9c466bc6654770bd2936d6ee9ff932
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536176B2
Reaction notes
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