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

HRID 1767937Notes

Reaction equation

HRID 1767937 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([OH:11])=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[CH3:12][C:13]1[N:14]=[C:15]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[S:16][C:17]=1[CH2:18][CH2:19]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>>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH2:19][CH2:18][C:17]3[S:16][C:15]([C:21]4[CH:22]=[CH:23][C:24]([C:27]([F:30])([F:28])[F:29])=[CH:25][CH:26]=4)=[N:14][C:13]=3[CH3:12])=[CH:8][CH:9]=2)[NH:4][CH:3]=1

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 136625956-HydroxyskatoleHCID 226475832-[4-Methyl-2-[4-(trifluoromethyl)phenyl]-5-thiazolyl]ethanol

Product 1

HCID 236144953-methyl-6-{2-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethoxy}-1H-indole

Procedure

In analogy to the procedure described in example 3 c], 3-methyl-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 3-methyl-6-{2-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethoxy}-1H-indole as yellow solid.

Sources & evidence

ORD record
ord-81bc1446db5a42f4865515cbdccebe1a
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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