N,N,N',N'-Tetramethylazodicarboxamide → HCID 131726504, compound

HRID 1767923Notes

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].O1C[CH2:23][CH2:22][O:21][CH:20]1[CH2:25][CH2:26][CH:27]([C:29]1[S:33][C:32]([C:34]2[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][CH:35]=2)=[N:31][C:30]=1[CH3:44])O.C(P(CCCC)CCCC)CCC.CN(C)[C:60](N=NC(N(C)C)=O)=[O:61]>>[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:27]([C:29]3[S:33][C:32]([C:34]4[CH:35]=[CH:36][C:37]([C:40]([F:42])([F:41])[F:43])=[CH:38][CH:39]=4)=[N:31][C:30]=3[CH3:44])[CH2:26][CH2:25][CH:20]3[CH2:60][O:61][CH2:23][CH2:22][O:21]3)[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 22647545HCID 22647545, compound

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

Product 1

HCID 131726504HCID 131726504, 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]-3-[1,3]dioxan-2-yl-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propan-1-ol in the presence of tributylphosphine and N,N,N′,N′-tetramethyl azodicarboxamide to obtain [rac]-(6-{3-dioxan-2-yl-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propoxy}-indol-1-yl)-acetic acid tert-butyl ester as yellow oil.

Sources & evidence

ORD record: ord-dc07631f485342a490b159296e2bb99f
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07235572B2

Reaction notes

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