Potassium Phosphate, Tribasic → HCID 16045371, compound

HRID 658275Notes

Reaction equation

HRID 658275 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]([CH:25]([CH3:27])[CH3:26])[C:12]1[CH:17]=[CH:16][C:15]([C:18]([OH:24])([CH3:23])[C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=1)(=[O:10])=[O:9].[CH:28]1(B(O)O)[CH2:30][CH2:29]1.[O-]P([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>[CH:28]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8]([N:11]([CH:25]([CH3:27])[CH3:26])[C:12]2[CH:17]=[CH:16][C:15]([C:18]([OH:24])([CH3:23])[C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=2)(=[O:10])=[O:9])[CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 69490242HCID 69490242, compound

Product 1

HCID 16045371HCID 16045371, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
95 °C

Procedure

To a vessel containing 2-bromo-N-isopropyl-N-(4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl)benzenesulfonamide (ii) (prepared as in Example 1, 0.020 g, 0.043 mmol), cyclopropylboronic acid (0.0070 g, 0.086 mmol), K3PO4 (0.018 g, 0.086 mmol), and Pd(PPh3)4 (0.0050 mg, 0.0043 mmol) under nitrogen atmosphere was added degassed toluene (0.40 mL) and H2O (0.040 mL). The vessel was sealed under nitrogen atmosphere and heated in a 95° C. oil bath for 17.5 h. The reaction was cooled to room temperature, diluted with CH2Cl2 (2 mL), and extracted with H2O (1 mL). The combined organics were dried with Na2SO4, concentrated in vacuo, and purified by silica gel chromatography (gradient elution 5-20% ethyl acetate in hexanes) to afford 25. 1H NMR (400 MHz, CDCl3) δ 0.85-0.090 (m, 2H), 1.10-1.19 (m, 8H), 1.78 (s, 3 H), 2.42 (bs, 1 H), 2.70-2.80 (m, 1 H), 4.53 (septet, J=6.7, 1H), 6.86 (d, J=7.8 Hz, 1H), 7.14 (t, J=7.3, 1H), 7.21 (d, J=8.6, 2H), 7.41 (t, J=7 Hz, 1 H), 7.53 (d, J=8.4 Hz, 2H), 7.84 (d, J=8 Hz, 1H).

Workup

  1. additionwas added
  2. customdegassed toluene (0.40 mL) and H2O (0.040 mL)
  3. customThe vessel was sealed under nitrogen atmosphere
  4. temperatureThe reaction was cooled to room temperature
  5. additiondiluted with CH2Cl2 (2 mL)
  6. extractionextracted with H2O (1 mL)
  7. dry with materialThe combined organics were dried with Na2SO4
  8. concentrationconcentrated in vacuo
  9. custompurified by silica gel chromatography (gradient elution 5-20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-3c5eaf0d9dbb4b9d8113fef3089f497f
Source dataset
uspto-grants-2011_12
Patent number
US08076376B2

Reaction notes

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