Tributyltin Chloride → 7-(5-Methylthiopyridin-3-yl)carbonyl-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole

HRID 1072336Notes

Reaction equation

HRID 1072336 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([CH:9]([OH:18])[C:10]2[N:11]=[CH:12][N:13]3[CH:17]=[CH:16][S:15][C:14]=23)[CH:6]=[N:7][CH:8]=1.[CH2:19]([Sn:23](Cl)([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH3:22].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1>[O-2].[O-2].[Mn+4]>[CH3:1][S:2][C:3]1[CH:4]=[C:5]([C:9]([C:10]2[N:11]=[CH:12][N:13]3[CH:17]=[C:16]([Sn:23]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:19][CH2:20][CH2:21][CH3:22])[S:15][C:14]=23)=[O:18])[CH:6]=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 223903167-[(5-Methylthiopyridin-3-yl)hydroxymethyl]imidazo[5,1-b]thiazoleHCID 23714775LiHMDS tetrahydrofuran

Product 1

HCID 223902287-(5-Methylthiopyridin-3-yl)carbonyl-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

A ketone compound (408 mg) was prepared in substantially the same manner as in step b) of Synthesis Example 1, except that 430 mg of 7-[(5-methylthiopyridin-3-yl)hydroxymethyl]imidazo[5,1-b]thiazole and 320 mg of manganese dioxide were used as the starting compounds. 7-(5-Methylthiopyridin-3-yl)carbonyl-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole (179 mg) was prepared in substantially the same manner as in step c) of Synthesis Example 1, except that 138 mg of the ketone compound, 0.300 ml of tri-n-butylstannyl chloride, and 2.25 ml of a 1.0 N lithium bis(trimethylsilyl)amide/THF solution were used as the starting materials.

Workup

  1. customof Synthesis Example 1
  2. customof Synthesis Example 1

Sources & evidence

ORD record
ord-2e85e86ecbf74aeaa0ac531a0ef3bec2
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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