Potassium Phosphate, Tribasic → HCID 86684309, compound

HRID 1411684Notes

Reaction equation

HRID 1411684 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:10](=[O:25])[N:11]([CH3:24])[CH:12]=[C:13](B3OC(C)(C)C(C)(C)O3)[CH:14]=2)[CH:5]=[C:4]([CH3:26])[N:3]=1.Cl[C:28]1[CH:33]=[CH:32][N:31]=[C:30]([N:34]2[CH2:45][CH2:44][N:43]3[C:36](=[CH:37][C:38]4[CH2:39][C:40]([CH3:47])([CH3:46])[CH2:41][C:42]=43)[C:35]2=[O:48])[C:29]=1[CH:49]=[O:50].C([O-])(=O)C.[Na+].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>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].C(#N)C.O>[CH3:46][C:40]1([CH3:47])[CH2:39][C:38]2[CH:37]=[C:36]3[N:43]([CH2:44][CH2:45][N:34]([C:30]4[C:29]([CH:49]=[O:50])=[C:28]([C:13]5[CH:14]=[C:9]([NH:8][C:6]6[CH:5]=[C:4]([CH3:26])[N:3]=[C:2]([CH3:1])[N:7]=6)[C:10](=[O:25])[N:11]([CH3:24])[CH:12]=5)[CH:33]=[CH:32][N:31]=4)[C:35]3=[O:48])[C:42]=2[CH2:41]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 86684310HCID 86684310, compound

Product 1

HCID 86684309HCID 86684309, compoundYield 80%

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 100-mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 173b (250 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), Pd(dppf)Cl2 (57 mg, 0.071 mmol), sodium acetate (19 mg, 1.4 mmol), K3PO4 (316 mg, 1.4 mmol), water (0.5 mL), and acetonitrile (15 mL). After three cycles of vacuum/argon flush, the mixture was heated at 100° C. for 3 h. After this time the reaction was filtered and the filtrate was evaporated in vacuo. The resulting residue was recrystallized from ethyl acetate to afford 173c as a brown solid (300 mg, 80%). MS-ESI: [M+H]+ 538.3.

Workup

  1. customA 100-mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
  2. customAfter three cycles of vacuum/argon flush
  3. filtrationAfter this time the reaction was filtered
  4. customthe filtrate was evaporated in vacuo
  5. customThe resulting residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1a0877684da74ca495b9cb8517ed4dbb
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

Loading…