Hydrochloric Acid → 5-(Butylsulfanyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1991099Notes

Reaction equation

HRID 1991099 reaction equation
C([Si](C)(C)[N:6]1[C:10]2=[N:11][CH:12]=[C:13]([S:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:14]=[C:9]2[CH:8]=[CH:7]1)(C)(C)C.Cl.C([O-])(O)=O.[Na+]>CO>[CH2:16]([S:15][C:13]1[CH:14]=[C:9]2[CH:8]=[CH:7][NH:6][C:10]2=[N:11][CH:12]=1)[CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 59128660HCID 59128660, compound

Product 1

HCID 591286855-(Butylsulfanyl)-1H-pyrrolo[2,3-b]pyridineYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude mixture containing 11 (5.38 g) was treated with MeOH (48 mL) and 10% aq. HCl (97 mL) for 0.5 h. The acid was neutralised by dropwise addition of sat. aqueous NaHCO3. The resulting solid was filtered off, washed with water (3×), dried in vacuum and extracted with CH2Cl2. The extracts were concentrated to afford a dark red oil, which was purified by SGC with CH2Cl2:MeOH as eluent (gradient elution up to 99:1, v/v) to give 12 as a brown oil (1.23 g, 37% over 2 steps); 1H NMR (400 MHz, CDCl3) δ 0.90 (t, J=7.3 Hz, 3H), 1.35-1.50 (m, 2H), 1.52-1.65 (m, 2H), 2.87 (t, J=7.4 Hz, 2H), 6.49 (dd, J=3.5, 1.8 Hz, 1H), 7.41 (dd, J=3.4, 2.3 Hz, 1H), 8.10 (d, J=2.0 Hz, 1H), 8.43 (d, J=2.0 Hz, 1H), 10.90-11.10 (bs, NH).

Workup

  1. filtrationThe resulting solid was filtered off
  2. washwashed with water (3×)
  3. customdried in vacuum
  4. extractionextracted with CH2Cl2
  5. concentrationThe extracts were concentrated
  6. customto afford a dark red oil, which
  7. customwas purified by SGC with CH2Cl2
  8. washMeOH as eluent (gradient elution up to 99:1

Sources & evidence

ORD record
ord-d6f6d20c63f54eab90627f0f0c1669cf
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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