4,7-Dibromo[1,2,5]thiadiazolo[3,4-c]pyridine → HCID 89286639, compound

HRID 929270Notes

Reaction equation

HRID 929270 reaction equation
[CH:1]1[N:9]=[C:8](Br)[C:7]2[C:3](=[N:4][S:5][N:6]=2)[C:2]=1[Br:11].[CH2:12]([C:28]1([CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH3:80])[C:51]2[CH:50]=[C:49]([Sn](CCCC)(CCCC)CCCC)[S:48][C:47]=2[C:30]2[S:31][C:32]([Sn:34]([CH2:43][CH2:44][CH2:45][CH3:46])([CH2:39][CH2:40][CH2:41][CH3:42])[CH2:35][CH2:36][CH2:37][CH3:38])=[CH:33][C:29]1=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[Br:11][C:2]1[C:3]2[C:7](=[N:6][S:5][N:4]=2)[C:8]([C:49]2[S:48][C:47]3[C:30]4[S:31][C:32]([Sn:34]([CH2:43][CH2:44][CH2:45][CH3:46])([CH2:35][CH2:36][CH2:37][CH3:38])[CH2:39][CH2:40][CH2:41][CH3:42])=[CH:33][C:29]=4[C:28]([CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH3:80])([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:51]=3[CH:50]=2)=[N:9][CH:1]=1

Participants

5

Reactant 2

HCID 581297894,7-Dibromo[1,2,5]thiadiazolo[3,4-c]pyridineHCID 89286619HCID 89286619, compound

Product 1

HCID 89286639HCID 89286639, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 4,7-dibromo-pyridal[2,1,3]thiadiazole (0.28 g, 0.95 mmol) and 1b (1.14 g, 0.95 mmol) in freshly distilled toluene (10 ml) was added Pd(PPh3)4 (109.8 mg, 0.095 mmol) under nitrogen, and then capped with a rubber septum. The reaction mixture was stirred at 75° C. for 10 hours. The solvent was removed and purified by column chromatography (silica was pretreated by 10 v/v % triethylamine/hexane solution) with hexane as eluent. The column separation was run for 3 times to give 268 mg of viscous purple oil, with yield of 25%. 1H NMR (500 MHz, CDCl3) δ (ppm): 8.92 (s, 1H), 8.49 (s, 1H), 7.39 (s, 1H), 2.21 (m, 4H), 1.77 (m, 6H), 1.54-1.25 (m, 68H), 1.12-1.01 (m, 15H). 13C NMR (125 MHz, CD2Cl2) δ (ppm): 163.10, 160.00, 156.32, 148.09, 147.92, 145.93, 144.00, 142.24, 141.83, 140.28, 129.79, 127.62, 106.17, 53.53, 37.86, 31.92, 29.97, 29.66, 29.63, 29.59, 29.54, 29.42, 29.39, 29.35, 29.32, 29.29, 29.02, 28.99, 27.21, 24.58, 22.69, 22.65, 13.88, 13.45, 10.96.

Workup

  1. customcapped with a rubber septum
  2. customThe solvent was removed
  3. custompurified by column chromatography (silica was pretreated by 10 v/v % triethylamine/hexane solution) with hexane as eluent
  4. customThe column separation

Sources & evidence

ORD record
ord-505d72b28a0a4c85bb8b938b9ca2cdfe
Source dataset
uspto-grants-2016_03
Patent number
US09293708B2

Reaction notes

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