Trimethylaluminum → HCID 66888773, compound

HRID 2069543Notes

Reaction equation

[CH3:1][Si:2]([CH3:24])([CH3:23])[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:18](OCC)=[O:19])[N:9]2[CH2:12][C:13]2[S:14][CH:15]=[CH:16][N:17]=2)=[CH:5][CH:4]=1.CC(C)(C)C([O:29][CH2:30][C:31]1[S:32][C:33]2[C:38]([N:39]=1)=[CH:37][C:36]([NH2:40])=[CH:35][N:34]=2)=O.C[Al](C)C>>[OH:29][CH2:30][C:31]1[S:32][C:33]2[C:38]([N:39]=1)=[CH:37][C:36]([NH:40][C:18]([C:8]1[N:9]([CH2:12][C:13]3[S:14][CH:15]=[CH:16][N:17]=3)[C:10]3[C:6]([CH:7]=1)=[CH:5][CH:4]=[C:3]([Si:2]([CH3:24])([CH3:23])[CH3:1])[CH:11]=3)=[O:19])=[CH:35][N:34]=2

Participants

Reactant 3

HCID 16682925Trimethylaluminum

HCID 58100934HCID 58100934, compound

HCID 58125487(6-Aminothiazolo[5,4-b]pyridin-2-yl)methyl pivalate

Product 1

HCID 66888773HCID 66888773, compoundYield 149.9%

Procedure

This compound was prepared according to a process similar to that described in step 16.2, by reacting 200 mg (0.523 mmol) of ethyl 6-trimethylsilyl-1-[(thiazol-2-yl)]methyl-1H-indole-2-carboxylate, prepared in the preceding step, with 178 mg (0.670 mmol) of (6-amino-thiazolo[5,4-b]pyrid-2-yl)methyl 2,2-dimethylpropanoate, obtained in step 4.2, in the presence of 0.39 mL (0.784 mmol) of a solution of trimethylaluminium (2M/toluene). The product was isolated by purification by chromatography on a column of silica, eluting with a mixture of dichloromethane and ethanol. 120 mg of the expected product are obtained.

Workup

customThis compound was prepared

Sources & evidence

ORD record: ord-de8dd40ac7c94d2d880d302f3df4be93
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299114B2

Reaction notes

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