2-(Tributylstannyl)-1,3-thiazole → HCID 22461301, compound

HRID 1937635Notes

Reaction equation

HRID 1937635 reaction equation
Br[C:2]1[C:10]2[C:9](=[O:11])[CH2:8][C:7]([CH3:13])([CH3:12])[CH2:6][C:5]=2[N:4]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][N:15]=2)[CH:3]=1.C([Sn](CCCC)(CCCC)[C:26]1[S:27][CH:28]=[CH:29][N:30]=1)CCC>>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([N:4]2[C:5]3[CH2:6][C:7]([CH3:13])([CH3:12])[CH2:8][C:9](=[O:11])[C:10]=3[C:2]([C:26]3[S:27][CH:28]=[CH:29][N:30]=3)=[CH:3]2)=[N:15][CH:16]=1

Participants

3

Reactant 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 22461259HCID 22461259, compound

Product 1

HCID 22461301HCID 22461301, compoundYield 37%

Procedure

In the same way as described in Example 15, Step 4 using 3-bromo-1-(5-chloropyridin-2-yl)-6,6-dimethyl-4,5,6,7-tetrahydroindol-4-one and 2-tributylstannylthiazole, the title compound (73 mg, 37%) was isolated as a pale yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 1.06 (6H,s), 2.44 (2H,s), 3.01 (2H,s), 7.63 (1H,d, J=3Hz), 7.80-7.84 (2H,m), 8.00 (1H,s), 8.20 (1H,dd, J=8.6 and 2.6 Hz), 8.69 (1H,d, J=2.6Hz). MS (ES+) 358/360 (M+1). 1H NMR (400 MHz, d6-DMSO) δ 1.02 (6H,s), 2.33 (2H,s), 2.97 (2H,s), 7.56 (1H,s), 7.71 (1H,d, J=8.6 Hz), 8.18 (1H,dd, J=8.7Hz and 2.6 Hz), 8.64 (1H,d, J=2.6 Hz). MS (ES+) 353/355 (M+1).

Sources & evidence

ORD record
ord-ba90c34795fc4031a92e04b764278037
Source dataset
uspto-grants-2002_05
Patent number
US06395766B1

Reaction notes

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