Triphenylphosphine → HCID 69280405, compound

HRID 1767949Notes

Reaction equation

HRID 1767949 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:19][C:20]1[S:24][C:23]([C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=2)=[N:22][C:21]=1[CH2:36]CO.[CH2:39](OC(C1SC(C2C=CC(OC(F)(F)F)=CC=2)=NC=1C)=O)C.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>>[C:1]([O:5][C:6](=[O:18])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:39][CH2:19][C:20]3[S:24][C:23]([C:25]4[CH:26]=[CH:27][C:28]([O:31][C:32]([F:33])([F:34])[F:35])=[CH:29][CH:30]=4)=[N:22][C:21]=3[CH3:36])[CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 5

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 16109175HCID 16109175, compoundHCID 22647499HCID 22647499, compoundHCID 69283069tert-Butyl (6-hydroxy-1H-indol-1-yl)acetate

Product 1

HCID 69280405HCID 69280405, compound

Procedure

In analogy to the procedure described in example 3 c], (6-hydroxy-indol-1-yl)-acetic acid tert-butyl ester (example 6 b]) was reacted with 2-[5-methyl-2-(4-trifluoromethoxy-phenyl)-thiazol-4-yl]-ethanol {prepared from 4-methyl-2-(4-trifluoromethoxy-phenyl)-thiazole-5-carboxylic acid ethyl ester (PCT Int. Appl. (2001), WO 2001040207 A1) in analogy to the procedures described in examples 19 b] to 19 f]} in the presence of triphenylphosphine and di-tert-butyl azodicarboxylate to yield (6-{2-[4-methyl-2-(4-trifluoromethoxy-phenyl)-thiazol-5-yl]-ethoxy}-indol-1-yl)-acetic acid tert-butyl ester as yellow oil.

Sources & evidence

ORD record
ord-50c66f16e7ac4553ad381a0e26490fa1
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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