Hydrochloric Acid → HCID 59699849, compound

HRID 901549Notes

Reaction equation

HRID 901549 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17]C4CCCCO4)=[CH:13][CH:12]=3)=[CH:9][N:8]([S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[C:5]2=[N:6][CH:7]=1.C1(S)C=CC=CC=1.Cl>ClCCl.CCOCC>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)=[CH:9][N:8]([S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)(=[O:25])=[O:26])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 59699892HCID 59699892, compound

Product 1

HCID 59699849HCID 59699849, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

575 g (1.09 mmol) of 5-bromo-3-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine was dissolved in 250 ml of dichloromethane. To this solution was added 2.50 g (3.53 mmol) of PS-thiophenol (Argonaut Technologies) and 1.5 ml of a 2 M solution of hydrochloric acid in ether. The mixture was stirred at room temperature for 3 hours before the resin was filtered off, washing extensively with dichloromethane. The filtrate was evaporated to afford 389 mg (877 μmol, 81%) of 4-[5-bromo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-phenol as a pale yellow solid. 1H-NMR (d6-DMSO) δ: 9.67 [1H] s, 8.52 [1H] d, 8.43 [IH] d, 8.11 [1H] s, 8.03 [2H] d, 7.58 [2H] d(m), 7.43 [2H] d, 6.89 [2H] d(m), 2.35 [3H] s. MS, m/z: 443 [MH+].

Workup

  1. filtrationwas filtered off
  2. washwashing extensively with dichloromethane
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-f74fa03e0dfb40dbb0dd9eab12ebbcb8
Source dataset
uspto-grants-2008_04
Patent number
US07361764B2

Reaction notes

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