Potassium Phosphate, Tribasic → HCID 86684362, compound

HRID 592830Notes

Reaction equation

HRID 592830 reaction equation
[CH:1]1([C:4]2N=[C:8]([NH:10][C:11]3[C:12](=[O:27])[N:13]([CH3:26])[CH:14]=[C:15](B4OC(C)(C)C(C)(C)O4)[CH:16]=3)[CH:7]=[CH:6][N:5]=2)[CH2:3][CH2:2]1.Cl[C:29]1[CH:34]=[CH:33][N:32]=[C:31]([N:35]2[CH2:46][CH2:45][N:44]3[C:37](=[CH:38][C:39]4[CH2:40][C:41]([CH3:48])([CH3:47])[CH2:42][C:43]=43)[C:36]2=[O:49])[C:30]=1[CH:50]=[O:51].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C:60]([O-])(=O)C.[Na+]>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.C(#N)C>[CH:1]1([C:4]2[CH:60]=[C:8]([NH:10][C:11]3[C:12](=[O:27])[N:13]([CH3:26])[CH:14]=[C:15]([C:29]4[CH:34]=[CH:33][N:32]=[C:31]([N:35]5[CH2:46][CH2:45][N:44]6[C:37](=[CH:38][C:39]7[CH2:40][C:41]([CH3:48])([CH3:47])[CH2:42][C:43]=76)[C:36]5=[O:49])[C:30]=4[CH:50]=[O:51])[CH:16]=3)[CH:7]=[CH:6][N:5]=2)[CH2:2][CH2:3]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 517045Sodium AcetateHCID 768540784-chloro-2-(7,7-dimethyl-1-oxo-1,3,4,6,7,8-hexahydro-2H-cyclopenta(4,5)pyrrolo(1,2-a)pyrazin-2-yl)nicotinaldehydeHCID 86684361HCID 86684361, compound

Product 1

HCID 86684362HCID 86684362, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A 50-mL round-bottomed flask equipped with a reflux condenser was charged with 196c (258 mg, 0.70 mmol), 4-chloro-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridine-3-carbaldehyde 108a (240 mg, 0.70 mmol), K3PO4 (297 mg, 1.4 mmol), sodium acetate (190 mg, 1.4 mmol), 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium(II) (29 mg, 0.035 mmol), acetonitrile (10 mL), and water (0.5 mL). After bubbling nitrogen through the mixture for 30 minutes, it was heated at 100° C. under N2 protection for 1 h. Analysis of reaction by LCMS showed completed conversion to the desired product. The mixture was cooled to room temperature and diluted with dichloromethane (20 mL) and water (20 mL). The aqueous layer was separated and extracted with dichloromethane (3×20 mL). The combined organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The dark residue was purified by silica-gel column chromatography eluting with dichloromethane/methanol (80/1 to 30/1) to afford 196d (220 mg, 57%) as yellow solid. MS-ESI: [M+H]+ 549

Workup

  1. customA 50-mL round-bottomed flask equipped with a reflux condenser
  2. customAfter bubbling nitrogen through the mixture for 30 minutes
  3. customAnalysis of reaction by LCMS

Sources & evidence

ORD record
ord-a31d5809565744238c79302bf53853fa
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

Loading…