Boron tribromide → HCID 178515837, compound

HRID 69172Notes

Reaction equation

HRID 69172 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[N:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]3[N:17]([C:19]([CH2:22][C:23]4[CH:24]=[C:25]5[C:30](=[CH:31][CH:32]=4)[N:29]=[CH:28][CH:27]=[CH:26]5)=[CH:20][N:21]=3)[N:18]=2)=[CH:9][CH:8]=1>C(Cl)Cl>[N:29]1[C:30]2[C:25](=[CH:24][C:23]([CH2:22][C:19]3[N:17]4[N:18]=[C:13]([C:10]5[CH:9]=[CH:8][C:7]([OH:6])=[N:12][CH:11]=5)[CH:14]=[CH:15][C:16]4=[N:21][CH:20]=3)=[CH:32][CH:31]=2)[CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 442081346-[6-(6-Methoxypyridin-3-yl)-imidazo[1,2-b]pyridazin-3-ylmethyl]-quinoline

Product 1

HCID 178515837HCID 178515837, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Boron tribromide (1364 mg, 5.44 mmol) was added to a suspension of 6-[6-(6-Methoxypyridin-3-yl)-imidazo[1,2-b]pyridazin-3-ylmethyl]-quinoline (Example 62, 200 mg, 0.544 mmol) in DCM (5 mL) at −78° C. The RM was stirred at −78° C. for 15 min and then allowed to reach rt. It was then stirred at rt for 68 h. The RM was filtered and the obtained solid was purified by reverse phase chromatography (water 0.1% TFA/acetonitrile +0.1% TFA). The resulting oil precipitated in TBME/MeOH to afford the title compound as a white powder (tR 4.21 min (conditions 4), MH+=354.3, 1H-NMR in DMSO-d6: 9.00 (m, 1H); 8.58 (m, 1H); 8.31 (m, 2H); 8.19 (dd, 1H); 8.05 (m, 4H); 7.92 (dd, 1H); 7.70 (dd, 1H); 6.54 (d, 1H); 4.65 (s, 2H)).

Workup

  1. customto reach rt
  2. stirringIt was then stirred at rt for 68 h
  3. filtrationThe RM was filtered
  4. customthe obtained solid was purified by reverse phase chromatography (water 0.1% TFA/acetonitrile +0.1% TFA)
  5. customThe resulting oil precipitated in TBME/MeOH

Sources & evidence

ORD record
ord-f9acde036acc428896a602e197ba51f8
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

Loading…