N,N,N',N'-Tetramethylazodicarboxamide → {6-[2-(3-Fluoro-4-trifluoromethyl-phenyl)-4-methyl-thiazol-5-ylmethoxy]-indol-1-yl}-acetic acid tert-butyl ester

HRID 1767976Notes

Reaction equation

HRID 1767976 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].[F:19][C:20]1[CH:21]=[C:22]([C:30]2[S:31][C:32]([CH2:36]O)=[C:33]([CH3:35])[N:34]=2)[CH:23]=[CH:24][C:25]=1[C:26]([F:29])([F:28])[F:27].C(P(CCCC)CCCC)CCC.CN(C)C(N=NC(N(C)C)=O)=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][CH2:36][C:32]3[S:31][C:30]([C:22]4[CH:23]=[CH:24][C:25]([C:26]([F:29])([F:27])[F:28])=[C:20]([F:19])[CH:21]=4)=[N:34][C:33]=3[CH3:35])[CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 18526219(2-(3-Fluoro-4-(trifluoromethyl)phenyl)-4-methylthiazol-5-yl)methanolHCID 69283069tert-Butyl (6-hydroxy-1H-indol-1-yl)acetate

Product 1

HCID 11156660{6-[2-(3-Fluoro-4-trifluoromethyl-phenyl)-4-methyl-thiazol-5-ylmethoxy]-indol-1-yl}-acetic acid tert-butyl ester

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-(3-fluoro-4-trifluoromethyl-phenyl)-4-methyl-thiazol-5-yl]-methanol [PCT Int. Appl. (2002), WO 0228434 A2] in the presence of tributylphosphine and N,N,N′,N′-tetramethyl azodicarboxamide to obtain {6-[2-(3-fluoro-4-trifluoromethyl-phenyl)-4-methyl-thiazol-5-ylmethoxy]-indol-1-yl}-acetic acid tert-butyl ester as light yellow gum.

Sources & evidence

ORD record
ord-26a1a75113754f7dbba40e2828bbf74b
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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