Tetrahydrofuran → HCID 178474204, compound

HRID 640838Notes

Reaction equation

HRID 640838 reaction equation
O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:23])[CH3:22])=[CH:16][CH:15]=3)=[O:13])[CH:10]=2)[NH:5][C:4]1=[O:24].[NH2:25][C:26]1[CH:27]=[CH:28][C:29](OC)=[C:30]([OH:32])[CH:31]=1.[CH2:35]1COCC1>>[OH:32][C:30]1[CH:31]=[C:26]([NH:25][CH:2]=[C:3]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([C:12]([C:14]4[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:23])[CH3:22])=[CH:16][CH:15]=4)=[O:13])[CH:10]=3)[NH:5][C:4]2=[O:24])[CH:27]=[CH:28][C:29]=1[CH3:35]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 743145-Amino-2-methoxyphenolHCID 178474207HCID 178474207, compound

Product 1

HCID 178474204HCID 178474204, compoundYield 63%

Conditions

Temperature
65 °C

Procedure

A small screw cap test tube was charged with N-[4-(3-Hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-acetamide (as prepared in Example 11, 50 mg, 0.155 mmol) and THF (2 mL). To the resulting solution was added 5-Amino-2-methoxy-phenol (21.0 mg, 0.170 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature. Hexanes were added to the reaction mixture. The solid precipitate that formed was washed with ˜1 mL of i-prOH yielding 63% (42 mg, 0.098 mmol) of the title compound.

Workup

  1. customA small screw cap test tube
  2. temperatureSubsequently, the reaction mixture was cooled to room temperature
  3. customThe solid precipitate that formed

Sources & evidence

ORD record
ord-75894c9dd1ff4bb2982ab8431c72ff54
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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