Phenylboronic Acid → HCID 18382745, compound

HRID 2297795Notes

Reaction equation

HRID 2297795 reaction equation
Br[C:2]1[S:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2Cl)[CH:3]=1.[NH2:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[CH:16]2.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>ClC(Cl)C.C(O)(C)(C)C>[NH:18]1[C:19]2[C:15](=[CH:14][C:13]([NH:12][C:8]3[CH:7]=[CH:6][N:5]=[C:4]4[CH:3]=[C:2]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[S:10][C:9]=34)=[CH:21][CH:20]=2)[CH:16]=[CH:17]1

Participants

6

Reactant 3

HCID 66827Phenylboronic AcidHCID 788675-AminoindoleHCID 183827742-Bromo-7-chlorothieno[3,2-b]pyridine

Product 1

HCID 18382745HCID 18382745, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
85 °C

Procedure

In a sealed tube 2-bromo-7-chloro-thieno[3,2-b]pyridine (1.01 g, 4.08 mmol) was dissolved in 15 mL of dichloroethane and 15 mL of t-butylalcohol. 5-Amino-indole (540 mg, 4.08 mmol) was added, the tube was sealed, and the contents were heated at 85° C. for 36 hours. The solution was cooled and filtered, the solid washed with methylene chloride, and dried in vacuo to afford 1.96 g of crude product. A portion of the material (100 mg, 0.29 mmol) was coupled with benzeneboronic acid in a procedure analogous to example 2 to afford 37.1 mg (38%) of (1H-indol-5-yl)-(2-phenyl-thieno[3,2-b]pyridin-7-yl)-amine. 1H NMR (400 MHz, DMSO) d 11.1 (s, 1H), 8.69 (s, 1H), 8.15 (d, 1H), 7.78 (m, 3H), 7.41 (m, 6H), 6.98 (d, 1H), 6.53 (d, 1H), 6.41 (s, 1H); LC-MS: 342 (MH+); HPLC RT: 4.81.

Workup

  1. customthe tube was sealed
  2. temperatureThe solution was cooled
  3. filtrationfiltered
  4. washthe solid washed with methylene chloride
  5. customdried in vacuo
  6. customto afford 1.96 g of crude product

Sources & evidence

ORD record
ord-0e4afc863b1541ca942aca2e3d000e57
Source dataset
uspto-grants-2002_12
Patent number
US06492383B1

Reaction notes

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