Phenyl carbamate → HCID 18005097, compound

HRID 1603802Notes

Reaction equation

HRID 1603802 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1.[C:16](=O)([O:18]C1C=CC=CC=1)N.[CH3:26][O:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][C:36]=1[C:37]([F:40])([F:39])[F:38])[NH:33][CH2:32][CH2:31]2>C(OCC)(=O)C>[CH3:26][O:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][C:36]=1[C:37]([F:40])([F:38])[F:39])[N:33]([C:16](=[O:18])[NH:13][C:12]1[CH:14]=[CH:15][C:9]([O:8][CH2:7][C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)=[CH:10][CH:11]=1)[CH2:32][CH2:31]2

Participants

5

Reactant 3

HCID 69322Phenyl carbamateHCID 112067135-Methoxy-6-(trifluoromethyl)indolineHCID 136883714-[(Pyridin-4-yl)methoxy]aniline

Product 1

HCID 18005097HCID 18005097, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(Pyridin-4-ylmethyloxy)aniline (0.5 g, 2.5 mmol) was converted to the phenyl carbamate and treated with 5-methoxy-6-trifluoromethylindoline (0.54 g, 2.5 mmol) as in the method of Example 52. Chromatography using ethyl acetate as eluant followed by recrystallisation from ethyl acetate/petroleum ether (60-80°) afforded the title compound (0.23 g, 24%) as an off-white crystalline solid m.p. 205-207° C.

Workup

  1. customfollowed by recrystallisation from ethyl acetate/petroleum ether (60-80°)

Sources & evidence

ORD record
ord-782caa8bf35344e88d3f47af54684d4e
Source dataset
uspto-grants-1999_11
Patent number
US05990133

Reaction notes

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