5-Bromo-benzo[2,1,3]thiadiazole → 5-[2-(Pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]benzo[2,1,3]thiadiazole

HRID 751285Notes

Reaction equation

HRID 751285 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]2=[N:6][S:7][N:8]=[C:4]2[CH:3]=1.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[C:18](B(O)O)=[C:19]2[CH2:24][CH2:23][CH2:22][N:20]2[N:21]=1>>[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[C:18]([C:2]2[CH:10]=[CH:9][C:5]3=[N:6][S:7][N:8]=[C:4]3[CH:3]=2)=[C:19]2[CH2:24][CH2:23][CH2:22][N:20]2[N:21]=1

Participants

3

Reactant 2

HCID 27762955-Bromo-benzo[2,1,3]thiadiazoleHCID 59710031(2-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-boronic acid

Product 1

HCID 117234765-[2-(Pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]benzo[2,1,3]thiadiazoleYield 24.5%

Procedure

In a similar fashion to Example 4, react 5-bromo-[2,1,3]-benzothiadiazole (Maybridge; 180 mg, 0.83 mmol) with 2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-boronic acid (Preparation 5; 190 mg, 0.83 mmol) to provide the title compound (65 mg, 16%) as a tan solid. Melting Range: 184-186° C. MS ESI+ m/e 320 (M+1). 1H NMR (CDCl3) δ 8.61-8.52 (m, 1H), 7.94 (s, 1H), 7.89-7.82 (m, 1H), 7.70-7.62 (m, 2H), 7.52-7.49 (m, 1H), 7.29-7.17 (m, 1H), 4.33-4.22 (m, 2H), 3.12-3.02 (m, 2H), 2.72-2.60 (m, 2H). HPLC: >99%, Rt=15.41 min. TLC (SiO2): Rf0.3 (1:1 [80:18-2 chloroform/methanol/concentrated aqueous ammonium hydroxide]/dichloromethane).

Sources & evidence

ORD record
ord-ff42b3a27830420b952143015c70bae0
Source dataset
uspto-grants-2008_07
Patent number
US07405299B2

Reaction notes

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