Toluene → HCID 49820901, compound

HRID 1897798Notes

Reaction equation

HRID 1897798 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:19])[C:9]([C:11]3[CH:12]=[C:13]([CH:17]=O)[CH:14]=[N:15][CH:16]=3)=[CH:10][C:5]2=[CH:4][CH:3]=1.[CH2:20]([S:22]([NH2:25])(=[O:24])=[O:23])[CH3:21].C1(C)C=CC=CC=1.[BH4-].[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].O.CO>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:19])[C:9]([C:11]3[CH:12]=[C:13]([CH2:17][NH:25][S:22]([CH2:20][CH3:21])(=[O:24])=[O:23])[CH:14]=[N:15][CH:16]=3)=[CH:10][C:5]2=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 73702EthanesulfonamideHCID 4311764Sodium borohydrideHCID 59578408HCID 59578408, compound

Product 1

HCID 49820901HCID 49820901, compound

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A 25 mL flask was charged with 5-(6-Chloro-1-methyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-pyridine-3-carbaldehyde (91 mg, 0.335 mmol), ethane sulfonamide (73.1 mg, 0.670 mmol) and toluene (5 mL). Titanium(IV) isopropoxide (0.147 mL, 0.502 mmol) was added dropwise. The mixture was stirred at 120° C. overnight. The mixture was concentrated in vacuo. The residue was taken up in DCM (5 mL) and MeOH (5 mL) and sodium borohydride (50.7 mg, 1.340 mmol) was added at 0° C. The mixture was stirred at 0° C. for 30 min. Water (1 mL) was added and the mixture was stirred for 5 min, then concentrated in vacuo. DMF (5 mL) was added and the suspension was filtered. The filtrate was purified by Xbridge RP 18 eluting with a 5 to 95 ACN-water gradient to afford ethanesulfonic acid [5-(6-chloro-1-methyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-pyridin-3-ylmethyl]-amide. ESI-MS: m/z 365.2 (M+H)+1H NMR (400 MHz, MeOD) δ ppm 1.38 (t, J=7.3 Hz, 2H), 3.23 (q, J=7.4 Hz, 2H), 4.08-4.17 (m, 2H), 4.59 (dd, J=8.8, 7.3 Hz, 2H), 7.10 (d, J=8.3 Hz, 1H), 7.53 (dd, J=8.6, 2.3 Hz, 1H), 7.63 (d, J=2.3 Hz, 1H), 7.92 (t, J=2.1 Hz, 1H), 8.40 (d, J=2.5 Hz, 1H), 8.56 (d, J=2.0 Hz, 2H)

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. stirringThe mixture was stirred at 0° C. for 30 min
  3. stirringthe mixture was stirred for 5 min
  4. concentrationconcentrated in vacuo
  5. additionDMF (5 mL) was added
  6. filtrationthe suspension was filtered
  7. customThe filtrate was purified by Xbridge RP 18 eluting with a 5 to 95 ACN-water gradient

Sources & evidence

ORD record
ord-4f1c2152e68b4efbb4b7a8bc5cf7c201
Source dataset
uspto-grants-2013_08
Patent number
US08519142B2

Reaction notes

Loading…