Potassium Phosphate, Tribasic → HCID 59464134, compound

HRID 1713731Notes

Reaction equation

HRID 1713731 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[O:12][C:13]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[F:23])=[N:14][N:15]=2)=[O:10])=[CH:4][CH:3]=1.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.O>[C:2]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[O:12][C:13]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[F:23])=[N:14][N:15]=2)=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 59464097HCID 59464097, compound2×

Product 1

HCID 59464134HCID 59464134, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

N-(4-Iodophenyl)-5-[(2-fluorophenyl)amino]-1,3,4-oxadiazole-2-carboxamide (Intermediate 35), 150 mg, 0.36 mmol), phenyl boronic acid (35 mg, 0.29 mmol), potassium phosphate (230 mg, 1.44 mmol), and tetrakis(triphenyl phosphine)palladium(0) (22 mg, 0.02 mmol) were stirred in DME (1.2 mL) and water (0.6 mL), in a microwave tube, and heated at 110° C. for 3 h. The reaction mixture was partitioned between ethyl acetate (10 mL) and water (10 mL), and extracted with ethyl acetate (2×10 mL). The organics were combined, and dried by passing through a Varian Chem elut column. The filtrate was concentrated in vacuo and purified by preparative HPLC to afford the title compound as a cream solid (25 mg, 19%):

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (10 mL) and water (10 mL)
  2. extractionextracted with ethyl acetate (2×10 mL)
  3. customdried
  4. concentrationThe filtrate was concentrated in vacuo
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-b9b54c19197d4da786f41d2cc941cc2a
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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