Tetrahydrofuran → HCID 178474204, compound

HRID 2352776Notes

Reaction equation

HRID 2352776 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-8a593491a98645e3a57de5e48b68365c
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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