Potassium Phosphate, Tribasic → HCID 86684322, compound

HRID 1411698Notes

Reaction equation

HRID 1411698 reaction equation
[CH3:1][N:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[C:4]([NH:17][C:18]2[CH:23]=[C:22]([CH3:24])[N:21]=[CH:20][N:19]=2)[C:3]1=[O:25].Cl[C:27]1[CH:32]=[CH:31][N:30]=[C:29]([N:33]2[CH2:44][CH2:43][N:42]3[C:35](=[CH:36][C:37]4[CH2:38][C:39]([CH3:46])([CH3:45])[CH2:40][C:41]=43)[C:34]2=[O:47])[C:28]=1[CH:48]=[O:49].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>[CH3:45][C:39]1([CH3:46])[CH2:38][C:37]2[CH:36]=[C:35]3[N:42]([CH2:43][CH2:44][N:33]([C:29]4[C:28]([CH:48]=[O:49])=[C:27]([C:6]5[CH:5]=[C:4]([NH:17][C:18]6[CH:23]=[C:22]([CH3:24])[N:21]=[CH:20][N:19]=6)[C:3](=[O:25])[N:2]([CH3:1])[CH:7]=5)[CH:32]=[CH:31][N:30]=4)[C:34]3=[O:47])[C:41]=2[CH2:40]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 86684323HCID 86684323, compound

Product 1

HCID 86684322HCID 86684322, compoundYield 47%

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 single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 180b (239 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 (239 mg 0.70 mmol), Pd(dppf)Cl2 (57 mg, 0.070 mmol), sodium acetate (115 mg, 1.4 mmol), K3PO4 (320 mg, 1.4 mmol), water (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 concentrated under reduced pressure. The resulting residue was purified by silica-gel column chromatography eluting with 40:1 dichloromethane/methanol to afford 180c as a yellow solid (170 mg, 47%). MS-ESI: [M+H]+ 524.2.

Workup

  1. customA 50-mL single-neck 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. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica-gel column chromatography
  6. washeluting with 40:1 dichloromethane/methanol

Sources & evidence

ORD record
ord-28e840954d1f4937a389c07eb9149a70
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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