Triphenylphosphine → 6-{2-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethoxy}-3-propyl-1H-indole

HRID 1767942Notes

Reaction equation

HRID 1767942 reaction equation
[CH2:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([OH:13])=[CH:10][CH:11]=2)[NH:6][CH:5]=1)[CH2:2][CH3:3].[CH3:14][C:15]1[N:16]=[C:17]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)[S:18][C:19]=1[CH2:20][CH2:21]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>>[CH3:14][C:15]1[N:16]=[C:17]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)[S:18][C:19]=1[CH2:20][CH2:21][O:13][C:9]1[CH:8]=[C:7]2[C:12]([C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][NH:6]2)=[CH:11][CH:10]=1

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 226475832-[4-Methyl-2-[4-(trifluoromethyl)phenyl]-5-thiazolyl]ethanolHCID 236144983-propyl-1H-indol-6-ol

Product 1

HCID 236145086-{2-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethoxy}-3-propyl-1H-indole

Procedure

In analogy to the procedure described in example 3 c], 3-propyl-1H-indol-6-ol was reacted with 2-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethanol (example 5 c]) in the presence of triphenylphosphine and di-tert-butyl azodicarboxylate to yield 6-{2-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethoxy}-3-propyl-1H-indole as yellow oil.

Sources & evidence

ORD record
ord-4232b2a3a0af4478a4b1a5c5bb4c764b
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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