2-(Tri-n-butylstannyl)thiophene → HCID 18406846, compound

HRID 1016425Notes

Reaction equation

HRID 1016425 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)CCC.Br[C:20]1[C:21]([O:36][CH2:37][C:38]2[N:39]([CH2:43][CH3:44])[N:40]=[CH:41][N:42]=2)=[N:22][N:23]2[C:28]=1[CH:27]=[N:26][N:25]=[C:24]2[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[F:35]>>[CH2:43]([N:39]1[C:38]([CH2:37][O:36][C:21]2[C:20]([C:6]3[S:7][CH:8]=[CH:9][CH:10]=3)=[C:28]3[N:23]([C:24]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[F:35])=[N:25][N:26]=[CH:27]3)[N:22]=2)=[N:42][CH:41]=[N:40]1)[CH3:44]

Participants

3

Reactant 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 18406952HCID 18406952, compound

Product 1

HCID 18406846HCID 18406846, compoundYield 59%

Procedure

This was prepared in 59% yield using a similar procedure to that described in Example 53 except using 2-(tributylstannyl)thiophene instead of 2-(tributylstannyl)pyridine and 3-bromo-2-(2-ethyl-2H-[1,2,4]triazol-3-ylmethoxy)-7-(2-fluorophenyl)pyrazolo[1,5-d][1,2,4]triazine instead of 3-bromo-7-(2-fluorophenyl)-2-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)-pyrazolo[1,5-d][1,2,4]triazine. Data for title compound: mp=190-192° C. (CH2Cl2-EtOAc); 1H NMR (360 MHz, CDCl3) δ 1.39 (3H, t, J=7.3 Hz), 4.18 (2H, q, J=7.3 Hz), 5.60 (2H, s), 7.15 (1H, m), 7.29 (1H, t, J=9.4 Hz), 7.38-7.42 (2H, m), 7.46 (1H, d, J=3.6 Hz), 7.66 (1H, m), 7.81 (1H, m), 7.90 (1H, s), 9.56 (1H, s); MS (ES+) m/e 422 [MH]+; Anal. Found C, 57.30; H, 3,71; N, 23.35%. C20H16FN7OS requires C, 57.00; H, 3.83; N, 23.26%.

Workup

  1. customThis was prepared in 59% yield

Sources & evidence

ORD record
ord-eaf2652862814b12a4891d4eddb81318
Source dataset
uspto-grants-2002_11
Patent number
US06476030B1

Reaction notes

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