Potassium Acetate → HCID 58171510, compound

HRID 1752325Notes

Reaction equation

HRID 1752325 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([CH:8]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH:16]3[CH:23]4[CH2:24][C:19]5([C:26]([O:28][CH3:29])=[O:27])[CH2:20][CH:21]([CH2:25][CH:17]3[CH2:18]5)[CH2:22]4)=[O:14])[CH2:9]2)=[N:6][CH:7]=1.I[C:31]1[CH:36]=[CH:35][N:34]([CH3:37])[C:33](=[O:38])[CH:32]=1.CC1(C)C(C)(C)OB(B2OC(C)(C)C(C)(C)O2)O1.CC([O-])=O.[K+]>CS(C)=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].O>[CH3:37][N:34]1[CH:35]=[CH:36][C:31]([C:2]2[CH:3]=[N:4][C:5]([CH:8]3[CH2:12][CH2:11][N:10]([C:13]([O:15][CH:16]4[CH:23]5[CH2:24][C:19]6([C:26]([O:28][CH3:29])=[O:27])[CH2:20][CH:21]([CH2:25][CH:17]4[CH2:18]6)[CH2:22]5)=[O:14])[CH2:9]3)=[N:6][CH:7]=2)=[CH:32][C:33]1=[O:38]

Participants

8

Reactant 4

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 534080094-Iodo-1-methylpyridin-2(1H)-oneHCID 58171533HCID 58171533, compound

Product 1

HCID 58171510HCID 58171510, compoundYield 146.2%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 1-(methoxycarbonyl)adamantan-4-yl 3-(5-bromopyrimidin-2-yl)pyrrolidine-1-carboxylate (24 mg, 0.05 mmol), 4-iodo-1-methylpyridin-2(1H)-one (25 mg, 0.1 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (38.1 mg, 0.15 mmol), KOAc (49 mg, 0.5 mmol) and Pd(dppf)Cl2 (1 mg, 0.001 mmol) in DMSO (5 mL) under nitrogen was heated to 100 C for 2 h. The reaction mixture was treated with water and extracted with EtOAc (10 mL×3). The combined organic layers were dried over sodium sulfate, filtered and concentrated to afford an oil which was purified by preparative TLC to afford 1-(methoxycarbonyl)adamantan-4-yl 3-(5-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)pyrimidin-2-yl)pyrrolidine-1-carboxylate (36 mg, 36%).

Workup

  1. extractionextracted with EtOAc (10 mL×3)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford an oil which
  6. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-2cc51ea794214aeb9e67af78f0b5d6fc
Source dataset
uspto-grants-2015_10
Patent number
US09163012B2

Reaction notes

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