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Potassium Phosphate, Tribasic → HCID 57454141, compound

HRID 546948
Notes
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Reaction equation

HRID 546948 reaction equation
C([Si](C)(C)[O:6][C:7]([C:42]([F:45])([F:44])[F:43])([C:38]([F:41])([F:40])[F:39])/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:21]2[CH:26]=[CH:25][C:24](B3OC(C)(C)C(C)(C)O3)=[C:23]([CH3:36])[CH:22]=2)([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:12][C:11]=1[CH3:37])(C)(C)C.[CH2:48]([O:50][C:51](=[O:60])[CH2:52][C:53]1[CH:54]=[N:55][C:56](Br)=[N:57][CH:58]=1)[CH3:49].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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.O>[CH2:48]([O:50][C:51](=[O:60])[CH2:52][C:53]1[CH:54]=[N:55][C:56]([C:24]2[CH:25]=[CH:26][C:21]([C:16]([CH2:19][CH3:20])([C:13]3[CH:14]=[CH:15][C:10](/[CH:9]=[CH:8]/[C:7]([OH:6])([C:42]([F:44])([F:45])[F:43])[C:38]([F:41])([F:40])[F:39])=[C:11]([CH3:37])[CH:12]=3)[CH2:17][CH3:18])=[CH:22][C:23]=2[CH3:36])=[N:57][CH:58]=1)[CH3:49]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 57443494Ethyl 2-(2-bromopyrimidin-5-yl)acetateHCID 57709023HCID 57709023, compound

Product 1

HCID 57454141HCID 57454141, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent

Conditions

Temperature
95.5 °C

Procedure

Degassed N,N-dimethylformamide (0.32 mL) was added to 2-[4-(1-{4-[(E)-3-(t-butyl-dimethyl-silanyloxy)-4,4,4-trifluoro-3-trifluoromethyl-1-butenyl]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (Example 77-(1); 35.8 mg, 0.0523 mmol), 2-bromopyrimidine-5-acetic acid ethyl ester (Example 43-(3); 37.3 mg, 0.152 mmol), tetrakis(triphenylphosphine)palladium (0) (29.8 mg, 0.0258 mmol) and potassium phosphate (48.7 mg, 0.229 mmol). After replacement with nitrogen, the mixture was heated while stirring at an external temperature of 91 to 100° C. for 10 hours. Water was added to the reaction mixture, followed by extraction with diethyl ether. The extract was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=4/1) to give the title compound (13 mg, 41%).

Workup

  1. customDegassed N,N-dimethylformamide (0.32 mL)
  2. temperatureAfter replacement with nitrogen, the mixture was heated
  3. extractionfollowed by extraction with diethyl ether
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-610b11214dc440febaf0223b2a15078a
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07935688B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes