Carbon Tetrachloride → HCID 68563958, compound

HRID 1517342Notes

Reaction equation

HRID 1517342 reaction equation
[C:1]([Cl:5])(Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.OC[CH2:27][S:28]([C:31]1[CH:32]=[C:33]2[C:37](=[CH:38][CH:39]=1)[N:36]([C:40]1[N:45]=[CH:44][N:43]=[C:42]([O:46][CH:47]3[CH2:52][CH2:51][N:50]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:49][CH2:48]3)[CH:41]=1)[CH2:35][CH2:34]2)(=[O:30])=[O:29]>ClCCl>[Cl:5][CH2:1][CH2:27][S:28]([C:31]1[CH:32]=[C:33]2[C:37](=[CH:38][CH:39]=1)[N:36]([C:40]1[N:45]=[CH:44][N:43]=[C:42]([O:46][CH:47]3[CH2:48][CH2:49][N:50]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:51][CH2:52]3)[CH:41]=1)[CH2:35][CH2:34]2)(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 68561425HCID 68561425, compound

Product 1

HCID 68563958HCID 68563958, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Carbon tetrachloride (58 μL, 0.601 mmol) and triphenylphosphine (52 mg, 0.198 mmol) were added to a dichloromethane (5 mL) solution of the tert-butyl 4-[(6-{5-[(2-hydroxyethyl)sulfonyl]indolin-1-yl}pyrimidin-4-yl)oxy]piperidine-1-carboxylate (49.9 mg, 0.0990 mmol) produced in Example 84, and the mixture was stirred overnight at room temperature. From the reaction solution, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1-7:3, V/V) to obtain the title compound as white foam (32.3 mg, yield: 62%).

Workup

  1. distillationFrom the reaction solution, the solvent was distilled off under reduced pressure
  2. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1-7:3, V/V)

Sources & evidence

ORD record
ord-77ae03bea4bd4800b4523718b0ad6edc
Source dataset
uspto-grants-2012_07
Patent number
US08232287B2

Reaction notes

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