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Triphenylphosphine → HCID 68899028, compound

HRID 735327
Notes
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Reaction equation

HRID 735327 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9](O)[CH:10]=[CH2:11].I[C:14]1[CH:19]=[C:18]([S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH:17]=[CH:16][C:15]=1[NH2:29].C(=O)([O-])O.[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)P(N(C)C)(N(C)C)=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[CH:11][C:16]2[C:15](=[CH:14][CH:19]=[C:18]([S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH:17]=2)[N:29]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 57421915HCID 57421915, compoundHCID 65416705HCID 65416705, compound

Product 1

HCID 68899028HCID 68899028, compoundYield 10.2%

Reagents, catalysts & solvents 3

HCID 167845
palladium(II) acetate
Catalyst
HCID 962WaterSolvent
HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
140 °C

Procedure

1-(2,4-Difluorophenyl)prop-2-en-1-ol (Step 3, 260 mg, 1.41 mmol), [2-iodo-4-(phenylsulfonyl)phenyl]amine (Step 2, 359 mg, 1 mmol), palladium acetate (22 mg, 0.1 mmol), sodium hydrogencarbonate (162 mg, 3 mmol) and triphenylphosphine (26 mg, 0.1 mmol) were combined in hexamethylphosphoramide (5 mL) and heated to 140° C. for 16 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine (x5), dried over MgSO4 and evaporated. The residue was purified by preparative HPLC to give the title compound (39 mg). 1H NMR (500 MHz, CDCl3) δ 8.59 (1H, d), 8.32 (1H, d), 8.21-8.14 (2H, m), 8.10 (1H, dd, J=2.1, 8.9 Hz), 8.03-7.98 (3H, m), 7.61-7.52 (3H, m), 7.09-7.05 (1H, m), 6.99-6.94 (1H, m).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine (x5)
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-3fdc9796593548c68e1eed9952289f3c
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07592456B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes