Potassium Phosphate, Tribasic → HCID 72799477, compound

HRID 2110240Notes

Reaction equation

HRID 2110240 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([NH:13][C:14]([C:16]1[CH:17]=[N:18][N:19]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=2[Cl:35])[C:20]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23](Br)[CH:22]=1)=[O:15])[CH2:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[S:44]1[CH:48]=[CH:47][C:46](B(O)O)=[CH:45]1>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:8][CH2:9][CH:10]([NH:13][C:14]([C:16]1[CH:17]=[N:18][N:19]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=2[Cl:35])[C:20]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:45]2[S:44][CH:48]=[CH:47][CH:46]=2)[CH:22]=1)=[O:15])[CH2:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 581760Thiophene-3-boronic acidHCID 76571654HCID 76571654, compound

Product 1

HCID 72799477HCID 72799477, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 281A (27 mg, 50 umol) in 1 mL dioxane was added 2M solution of K3PO4 (100 uL), Pd(PPh3)4 (3 mg, 2 umol) and the contents were degassed and purged with nitrogen. To this solution was added 3-thiophene boronic acid (7 mg, 55 umol) and the resulting mixture was heated in a sealed 1 dram vial at 110° C. for 48 h. Contents were cooled to room temperature and passed through a waters HLB u elution plate to get rid of insoluble material and the filtrate was further purified via prep HPLC (Xterra 10×50 mm, S5 column, MeOH— Water gradient) to give the title compound. HPLC retention time (2.04 min). Observed mass 576.13.

Workup

  1. customthe contents were degassed
  2. custompurged with nitrogen
  3. temperatureContents were cooled to room temperature
  4. washpassed through a waters HLB u elution plate
  5. customto get rid of insoluble material
  6. customthe filtrate was further purified via prep HPLC (Xterra 10×50 mm, S5 column, MeOH— Water gradient)

Sources & evidence

ORD record
ord-e09fe466252f49cbb4d2cebf59cc5deb
Source dataset
uspto-grants-2009_04
Patent number
US07517900B2

Reaction notes

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