1-Methanesulfonyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine → 4-[5-(1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-furo[2,3-c]pyridin-2-yl]-4-methyl-piperidine-1-carboxylic acid tert-butyl ester

HRID 1471800Notes

Reaction equation

HRID 1471800 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[O:24][C:18]3=[CH:19][N:20]=[C:21](Cl)[CH:22]=[C:17]3[CH:16]=2)([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:25][S:26]([N:29]1[CH2:34][CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH2:31][CH2:30]1)(=[O:28])=[O:27]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[O:24][C:18]3=[CH:19][N:20]=[C:21]([C:32]4[CH2:33][CH2:34][N:29]([S:26]([CH3:25])(=[O:28])=[O:27])[CH2:30][CH:31]=4)[CH:22]=[C:17]3[CH:16]=2)([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 679734971-Methanesulfonyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridineHCID 866945764-(5-Chloro-furo[2,3-c]pyridin-2-yl)-4-methyl-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 866945874-[5-(1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-furo[2,3-c]pyridin-2-yl]-4-methyl-piperidine-1-carboxylic acid tert-butyl ester

Procedure

The title compound is prepared from 4-(5-chloro-furo[2,3-c]pyridin-2-yl)-4-methyl-piperidine-1-carboxylic acid tert-butyl ester and 1-methanesulfonyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,2,3,6-tetrahydro-pyridine following a procedure analogous to that described for Example 1; the reaction is conducted at 150° C. LC (method 4): tR=1.58 min; Mass spectrum (ESI+): m/z=476 [M+H]+.

Workup

  1. customis conducted at 150° C

Sources & evidence

ORD record
ord-caab6994d0034df18ceea0b904ebeeef
Source dataset
uspto-grants-2015_04
Patent number
US09012456B2

Reaction notes

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