7-Chloro-2-iodothieno(3,2-b)pyridine → HCID 22143687, compound

HRID 1825070Notes

Reaction equation

HRID 1825070 reaction equation
[CH3:1][N:2]1[C:6]([Sn](C)(C)C)=[CH:5][CH:4]=[N:3]1.[Cl:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]2[CH:18]=[C:19](I)[S:20][C:13]=12>CC1C=CC=CC=1C.C1(C)C=CC=CC=1.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>[Cl:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]2[CH:18]=[C:19]([C:6]3[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=3)[S:20][C:13]=12

Participants

6

Reactant 2

HCID 177504007-Chloro-2-iodothieno(3,2-b)pyridineHCID 22143620HCID 22143620, compound

Product 1

HCID 22143687HCID 22143687, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 7237O-XyleneSolvent

Procedure

A mixture of 1-methyl-5-trimethylstannanyl-1H-pyrazole 10a (2.1 g, 8.5 mmole), 7-chloro-2-iodo-thieno[3,2-b]pyridine (2.5 g, 8.5 mmole), tetrakis(triphenylphosphine)palladium(0) (0.5 g, 0.4 mmole, 5 mol %) in o-xylene (85 ml was degassed, purged with nitrogen and heated to 120°, which gave an orange solution. After 14 hours the black reaction mixture was diluted with toluene (100 ml) and extracted with 1.2 M HCl (3×60 ml). The combined aqueous layers were washed with toluene (100 ml). The organic layers were discarded and the aqueous layer was treated with NaOH to pH 14. The resultant white solid was collected (1.1 g, 52%): TLC (6% methanol-dichloromethane) Rf 0.8; 1H-NMR (DMSO-d6, 400 MHz) δ 8.70 (1H, d, J=5.3 Hz), 8.00 (1H, s), 7.63 (1H,d, J=5.3 Hz), 7.56 (1H, d, J=2.0 Hz), 6.79 (1H, d, J=2.0 Hz), 4.09 (3H, s). ESIMS m/z 250 (M+H)+.

Workup

  1. customwas degassed
  2. custompurged with nitrogen
  3. temperatureheated to 120°
  4. customwhich gave an orange solution
  5. extractionextracted with 1.2 M HCl (3×60 ml)
  6. washThe combined aqueous layers were washed with toluene (100 ml)
  7. additionthe aqueous layer was treated with NaOH to pH 14
  8. customThe resultant white solid was collected (1.1 g, 52%)

Sources & evidence

ORD record
ord-5274bedf59ad469fa9832c943327270e
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

Loading…