Potassium Phosphate, Tribasic → HCID 59464060, compound

HRID 1713806Notes

Reaction equation

HRID 1713806 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].I[C:10]1[CH:11]=[C:12]([N:16]([CH2:45][O:46][CH2:47][CH2:48][Si:49]([CH3:52])([CH3:51])[CH3:50])[C:17]2[O:21][C:20]([C:22]([N:24]([C:33]3[CH:34]=[N:35][C:36]([N:39]4[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)=[CH:37][CH:38]=3)[CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])=[O:23])=[N:19][N:18]=2)[CH:13]=[CH:14][CH:15]=1.[C:53]1(B(O)O)[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1>CN(C=O)C.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>[C:10]1([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[CH:15]=[CH:14][CH:13]=[C:12]([N:16]([CH2:45][O:46][CH2:47][CH2:48][Si:49]([CH3:52])([CH3:51])[CH3:50])[C:17]2[O:21][C:20]([C:22]([N:24]([C:33]3[CH:34]=[N:35][C:36]([N:39]4[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)=[CH:37][CH:38]=3)[CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])=[O:23])=[N:19][N:18]=2)[CH:11]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic Acid2×HCID 59464110HCID 59464110, compound

Product 1

HCID 59464060HCID 59464060, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Potassium phosphate (214 mg, 1.01 mmol) was added to 5-((3-iodophenyl){[2-(trimethylsilyl)ethoxy]methyl}amino)-N-(6-morpholin-4-ylpyridin-3-yl)-N-{[2-(trimethylsilyl)ethoxy]methyl}-1,3,4-oxadiazole-2-carboxamide (190 mg, 0.25 mmol) and phenylboronic acid (37 mg, 0.30 mmol) in DMF (3 mL) and the mixture was degassed. Tetrakis(triphenylphosphine)palladium (29 mg, 0.03 mmol) was added and the mixture was heated to 80° C. for 90 minutes. Phenylboronic acid (8 mg, 0.06 mmol) and tetrakis(triphenylphosphine)palladium (10 mg, 0.01 mmol) was added, the mixture degassed and heated to 80° C. for 240 minutes. The mixture was cooled, diluted with ether (60 mL) and washed with water (3×20 mL). The aqueous layers were re-extracted with ether (20 mL) and the organic layers were combined, dried and concentrated by evaporation. The residue was purified by chromatography, eluting with 0-20% ether/DCM to give the title compound (Intermediate 49, 149 mg, 84%) as a gum; 1H NMR δ 8.09 (1H, s), 7.83-7.66 (4H, m), 7.66-7.37 (6H, m), 6.86 (1H, d), 5.37 (2H, s), 5.19 (2H, s), 3.79-3.62 (8H, m), 3.55-3.49 (4H, m), 0.93 (4H, t), 0.06 (9H, s), 0.01 (9H, s).

Workup

  1. customthe mixture was degassed
  2. customthe mixture degassed
  3. temperatureheated to 80° C. for 240 minutes
  4. temperatureThe mixture was cooled
  5. additiondiluted with ether (60 mL)
  6. washwashed with water (3×20 mL)
  7. extractionThe aqueous layers were re-extracted with ether (20 mL)
  8. customdried
  9. concentrationconcentrated by evaporation
  10. customThe residue was purified by chromatography
  11. washeluting with 0-20% ether/DCM

Sources & evidence

ORD record
ord-eef2f76d3af24993991ed22318397ce8
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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