Sodium Hydroxide → HCID 9925094, compound

HRID 1791415Notes

Reaction equation

HRID 1791415 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:17]=[C:16]3[C:12]([C:13]([C:20](=[O:26])[C:21]([O:23]CC)=[O:22])=[CH:14][N:15]3[CH2:18][CH3:19])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[OH-].[Na+].FC(F)(F)C1C=CC(C2C=C3C(C(C(=O)C([O-])=O)=CN3CC)=CC=2)=CC=1>CO>[CH2:18]([N:15]1[C:16]2[C:12](=[CH:11][CH:10]=[C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:27])([F:1])[F:28])=[CH:8][CH:7]=3)[CH:17]=2)[C:13]([C:20](=[O:26])[C:21]([OH:23])=[O:22])=[CH:14]1)[CH3:19]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 22032908HCID 22032908, compoundHCID 86760139HCID 86760139, compound

Product 1

HCID 9925094HCID 9925094, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following the procedure described in Step 4 of Example 2, using ethyl 2-[6-(4-trifluoromethylphenyl)-1-ethyl-1H-indol-3-yl]-2-oxoacetate (0.0987 g, 0.253 mmol), and 1N sodium hydroxide (0.76 mL, 0.76 mmol) in methanol (5 mL), 2-[6-(4-trifluoromethylphenyl)-1-ethyl-1H-indol-3-yl]-2-oxoacetate acid (0.0714 g, 78%) was prepared as a yellow solid, mp 247-248° C. Mass spectrum (+APCI, [M+H]+) m/z 362; 1HNMR (400 MHz, DMSO-d6): δ 13.7-14.1 (br s, 1H), 8.55 (s, 1H), 8.3 (d, 1H, J=8.3 Hz), 8.05 (d, 1H, J=0.98 Hz), 8.0 (d, 2H, J=8.1 Hz), 7.8 (d, 2H, J=8.5 Hz), 7.7 (dd, 1H, J=8.5 Hz and 1.6 Hz), 4.45 (q, 2H, J=7.2 Hz), and 1.45 ppm (t, 3H, J=7.2 Hz).

Workup

  1. customwas prepared as a yellow solid, mp 247-248° C

Sources & evidence

ORD record
ord-7509f087bdc9406885e12a17f0944485
Source dataset
uspto-grants-2006_07
Patent number
US07074817B2

Reaction notes

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