N,N,N',N'-Tetramethylazodicarboxamide → HCID 69283055, compound

HRID 1767953Notes

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].[C:19]([Si:23]([CH3:47])([CH3:46])[O:24][CH2:25][CH2:26][CH2:27][CH:28]([C:30]1[S:34][C:33]([C:35]2[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][CH:36]=2)=[N:32][C:31]=1[CH3:45])O)([CH3:22])([CH3:21])[CH3:20].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][CH:28]([C:30]3[S:34][C:33]([C:35]4[CH:36]=[CH:37][C:38]([C:41]([F:43])([F:42])[F:44])=[CH:39][CH:40]=4)=[N:32][C:31]=3[CH3:45])[CH2:27][CH2:26][CH2:25][O:24][Si:23]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:47])[CH3:46])[CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 4

HCID 4278N,N,N',N'-Tetramethylazodicarboxamide

HCID 13831Tributylphosphine

HCID 23614513HCID 23614513, compound

HCID 69283069tert-Butyl (6-hydroxy-1H-indol-1-yl)acetate

Product 1

HCID 69283055HCID 69283055, 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 [rac]-4-(tert-butyl-dimethyl-silanyloxy)-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-butan-1-ol in the presence of tributylphosphine and N,N,N′,N′-tetramethyl azodicarboxamide to obtain [rac]-(6-[4-(tert-butyl-dimethyl-silanyloxy)-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-butoxy}-indol-1-yl)-acetic acid tert-butyl ester as yellow oil.

Sources & evidence

ORD record: ord-d3286b636a4d497691a30b41bb35b7b8
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07235572B2

Reaction notes

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