2-Chloropyridine-4-boronic acid → [1-(2-Chloro-pyridin-4-yl)-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(1,1-dioxo-1lambda6-thiomorpholin-4-yl)-methanone

HRID 493996Notes

Reaction equation

HRID 493996 reaction equation
[O:1]=[S:2]1(=[O:29])[CH2:7][CH2:6][N:5]([C:8]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([O:19][CH:20]2[CH2:25][CH2:24][N:23]([CH:26]([CH3:28])[CH3:27])[CH2:22][CH2:21]2)=[CH:14][CH:13]=3)=[O:9])[CH2:4][CH2:3]1.[Cl:30][C:31]1[CH:36]=[C:35](B(O)O)[CH:34]=[CH:33][N:32]=1>>[Cl:30][C:31]1[CH:36]=[C:35]([N:11]2[C:12]3[C:17](=[CH:16][C:15]([O:19][CH:20]4[CH2:25][CH2:24][N:23]([CH:26]([CH3:27])[CH3:28])[CH2:22][CH2:21]4)=[CH:14][CH:13]=3)[CH:18]=[C:10]2[C:8]([N:5]2[CH2:6][CH2:7][S:2](=[O:1])(=[O:29])[CH2:3][CH2:4]2)=[O:9])[CH:34]=[CH:33][N:32]=1

Participants

3

Reactant 2

HCID 51515952-Chloropyridine-4-boronic acidHCID 16739577(1,1-Dioxo-thiomorpholin-4-yl)-[5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-methanone

Product 1

HCID 16739647[1-(2-Chloro-pyridin-4-yl)-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(1,1-dioxo-1lambda6-thiomorpholin-4-yl)-methanone

Procedure

In analogy to the procedure described for the synthesis of example 5, the title compound was synthesized from (1,1-dioxo-thiomorpholin-4-yl)-[5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-methanone (Example 2) and 2-chloropyridine-4-boronic acid. The desired product was obtained in a yield of 8% as an off-white solid. MS (m/e): 531.5 (M+, 100%).

Workup

  1. customIn analogy to the procedure described for the synthesis of example 5

Sources & evidence

ORD record
ord-3448f9ff8d13425d8760168761eca92d
Source dataset
uspto-grants-2009_05
Patent number
US07538101B2

Reaction notes

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