Sodium Carbonate → tert-butyl 4-(2-(4-(benzo[d]thiazol-2-ylamino)phenoxy)pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 410194Notes

Reaction equation

HRID 410194 reaction equation
Br[C:2]1[C:3]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[S:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[C:25]([O:29][C:30]([N:32]1[CH2:37][CH:36]=[C:35](B(O)O)[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[S:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=[C:16]1[NH:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:3]2[C:2]([C:35]3[CH2:36][CH2:37][N:32]([C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:31])[CH2:33][CH:34]=3)=[CH:7][CH:6]=[CH:5][N:4]=2)=[CH:10][CH:11]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 21931462(1-(tert-Butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)boronic acidHCID 59326883N-(4-(3-bromopyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine

Product 1

HCID 59327027tert-butyl 4-(2-(4-(benzo[d]thiazol-2-ylamino)phenoxy)pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a round-bottomed flask was added N-(4-(3-bromopyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine (0.5770 g, 1.449 mmol), 1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-ylboronic acid (0.987 g, 4.35 mmol), PdCl2(dppf) (0.080 g, 0.145 mmol), and sodium carbonate (0.768 g, 7.24 mmol) in DME (3.62 mL) and Water (1.207 mL) at 80° C. to stir overnight. Reaction allowed to cool to room temperature. Solvent was removed. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep® pre-packed silica gel column (40 g), eluting with a gradient of 5% to 80% EtOAc in hexane, to provide tert-butyl 4-(2-(4-(benzo[d]thiazol-2-ylamino)phenoxy)pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate. MS (ESI, pos. ion) m/z: 501.0 (M+1).

Workup

  1. customReaction
  2. customSolvent was removed
  3. customchromatographed through a Redi-Sep® pre-packed silica gel column (40 g)
  4. washeluting with a gradient of 5% to 80% EtOAc in hexane

Sources & evidence

ORD record
ord-64c9a69de6a54231bcb44a35ce98d70c
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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