Trifluoroacetic acid → HCID 17980107, compound

HRID 1766232Notes

Reaction equation

HRID 1766232 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[C:19]2[C:25]1[CH2:26][CH2:27][N:28]([CH3:31])[CH2:29][CH:30]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([SiH](CC)CC)C>C(Cl)Cl>[CH2:8]([O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[C:19]2[CH:25]1[CH2:26][CH2:27][N:28]([CH3:31])[CH2:29][CH2:30]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 12229248HCID 12229248, compound

Product 1

HCID 17980107HCID 17980107, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By a method similar to Preparation 20, using trifluoroacetic acid (1.6 mL), 5-benzyloxy-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (222 mg, 0.7 mmol), methylene chloride (3 mL) and triethylsilane (111 μL, 0.7 mmol) gave the tile compound as a yellow foam (210 mg) which was crystallized from ethyl acetate to give 160 mg of pale yellow crystals: mp=163-164° C.; MS(m/e): 321 (M+1), 379 (M+59); Calculated for C21H24N2O: Calcd: C, 78.72; H, 7.55; N, 8.74. Found: C, 78.63; H, 7.64; N, 8.78.

Workup

  1. customBy a method similar to Preparation 20

Sources & evidence

ORD record
ord-addf49c29cd540a595742bac2a59ed6d
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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